[ CAS No. 122-03-2 ] {[proInfo.proName]}

Name: 122-03-2|4-Isopropylbenzaldehyde|97%
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3d Animation Molecule Structure of 122-03-2

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Quality Control of [ 122-03-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 122-03-2 ]

SDS Specification

Alternatived Products of [ 122-03-2 ]

Product Details of [ 122-03-2 ]

CAS No. :	122-03-2	MDL No. :	MFCD00006953
Formula :	C₁₀H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WTWBUQJHJGUZCY-UHFFFAOYSA-N
M.W :	148.20	Pubchem ID :	326
Synonyms :	4-Isopropylbenzaldehyde;Cuminal;Cuminic aldehyde	Chemical Name :	4-Isopropylbenzaldehyde

Calculated chemistry of [ 122-03-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.41
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	2.4
Log Po/w (SILICOS-IT) :	2.96
Consensus Log Po/w :	2.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.444 mg/ml ; 0.003 mol/l
Class :	Soluble
Log S (Ali) :	-2.37
Solubility :	0.634 mg/ml ; 0.00428 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.15
Solubility :	0.105 mg/ml ; 0.000711 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 122-03-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 122-03-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 122-03-2 ]
Downstream synthetic route of [ 122-03-2 ]

[ 122-03-2 ] Synthesis Path-Upstream 1~10

1
[ 122-03-2 ]
[ 88371-24-8 ]

Reference： [1] Chemische Berichte, 1889, vol. 22, p. 2279[2] Chemische Berichte, 1890, vol. 23, p. 3086

2
[ 122-03-2 ]
[ 73789-86-3 ]

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 38, p. 6681 - 6683
[2] Patent: WO2013/159095, 2013, A1,

3
[ 122-03-2 ]
[ 2051-18-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; Inert atmosphere; Schlenk technique; Glovebox Stage #2: With thionyl chloride In dichloromethane at 5 - 20℃; Inert atmosphere; Schlenk technique; Glovebox	500 ml of methanol was added dropwise by vigorous stirring over 5 h to a mixture of 148 g (1.0 mol) 4-isopropylbenzaldehyde and 37.8 g (1.0 mol) of NaBH₄ in 1000 ml of THF at 0-5 °C. This mixture was stirred overnight at room temperature and then evaporated under vacuum. The residue was acidified with 1200 ml of 2 M HC1 to pH~l, and the formed (4-isopropylphenyl)methanol was extracted with 3 x 400 ml of dichloromethane. The combined organic extract was dried over Na₂SO₄ and evaporated to dryness. To the residue dissolved in 1000 ml of dichloromethane 73 ml (1.0 mol) of thionyl chloride was added dropwise at +5°C. The resulting solution was stirred at room temperature overnight, evaporated to dryness, and then the residue was dissolved in 750 ml dichloromethane. The formed solution was washed by 250 ml of water. The organic layer was separated, the aqueous layer was extracted with 2 x 150 ml of dichloromethane. The combined organic extract was dried over a₂S0₄, passed through a short pad of silica gel 60 (40-63 μιη), and evaporated to dryness. Crude product was distilled under vacuum to give 142 g (84percent) of a colorless liquid, b.p. 107-1 12 °C/15 mm Hg.

Reference： [1] Patent: WO2014/96282, 2014, A1, . Location in patent: Page/Page column 54

4
[ 1122-91-4 ]
[ 77047-87-1 ]
[ 28785-06-0 ]
[ 122-03-2 ]

Reference： [1] Chemical Communications, 2011, vol. 47, # 18, p. 5181 - 5183

5
[ 21047-57-4 ]
[ 122-03-2 ]
[ 23152-99-0 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 16, p. 4070 - 4073

6
[ 122-03-2 ]
[ 23152-99-0 ]

Reference： [1] Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 11, p. 1023 - 1027

7
[ 122-03-2 ]
[ 38628-51-2 ]

Reference： [1] Chemische Berichte, 1889, vol. 22, p. 2279[2] Chemische Berichte, 1890, vol. 23, p. 3086

8
[ 122-03-2 ]
[ 82657-71-4 ]

Reference： [1] Journal of the Chemical Society, 1956, p. 2455,246
[2] Journal of the Chemical Society, 1954, p. 2351

9
[ 122-03-2 ]
[ 100987-89-1 ]

Reference： [1] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491

10
[ 141-82-2 ]
[ 122-03-2 ]
[ 117391-53-4 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9152 - 9157
[2] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1356 - 1365

[ 122-03-2 ] Synthesis Path-Downstream 1~109

1
[ 110-89-4 ]
[ 534-59-8 ]
[ 122-03-2 ]
[ 101276-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Gensler; Berman [Journal of the American Chemical Society, 1958, vol. 80, p. 4949,4952]

2
[ 126-81-8 ]
[ 122-03-2 ]
3,4,6,7-tetrahydro-9-(4-isopropylphenyl)-3,3,6,6-tetramethyl-2H-xanthene-1,8-(5H,9H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With multiwalled carbon nanotube supported butyl 1-sulfonic acid; In ethanol; at 20℃; for 0.6h;	General procedure: A mixture of an aldehyde (2 mmol), dimedone (0.28g, 2 mmol), MWCNT-BuSO3H (0.066 g, 0.07 mmol), and ethanol (3 mL) was stirred for an appropriate time at room temperature. After completion of the reaction (monitoredby TLC), the catalyst was filtered off and washed with ethanol (2 × 10 mL). Then, the filtrate was concentrated on a rotary evaporator under reduced pressure and the crude product recrystallized from ethanol. All productsare known compounds and were identified by comparison of their physical and spectral data with those ofthe authentic samples.
94%	With sulfonated polyethylene glycol; In neat (no solvent); at 80℃; for 2.66667h;Green chemistry;	General procedure: 5,5-dimethyl-1,3-cyclohexanedione (2 mmol) and aromaticaldehyde (1 mmol) were mixed with PEG-SO3H (1.2 g,0.2 mmol) and the obtained mixture was stirred magneticallyat 80C. After the completion of reaction (as monitored byTLC) warm water (5 mL) was added and the mixture stirredfor about 5 min. The insoluble crude product was filteredand recrystallized from EtOH and the pure product wasobtained. In order to recover the catalyst, the filtratewas dried under reduced pressure and recovered catalyst waswashed with diethyl ether and reused after drying underreduced pressure.
92%	With sulfated zirconia (SO42-/ZrO2); In ethanol; at 70℃; for 8h;	General procedure: The SO 42-/ZrO 2 catalyst (15 wt%) was added to a solution of anaromatic aldehyde (1 mmol) and 5,5-dimethyl-1,3-cyclohexanedione(dimedone) (2 mmol) in ethanol (3 mL). The mixture was heated at70 C for 8-15 h and the reaction was monitored by TLC. Aftercompletion of the reaction, the catalyst was separated by ltration,the ltrate dried over anhydrous Na 2 SO 4 and concentrated to dryness.The 1,8-dioxo-octahydroxanthene product was recrystallized fromethanol. All detected products were characterized by comparison oftheir spectral and physical data with those of reported in literature[15,19,20-27].

90%	With bis-2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepiniumethyl disulfate; In neat (no solvent); at 120℃; for 0.2h;Green chemistry;	General procedure: A mixture of cyclic 1,3-dicarbonyl (2 mmol), aldehydes (1 mmol), and [DBU]2[EDS] (40 mol%) was stirred at 120 C in oil bath for the time show in Table 2. Upon completion of the reaction as indicated by TLC (hexane:ethyl acetate, 8:2), hot EtOH (96%,1 ml) was added to the mixture which was stirred for 2 min. Then the reaction mixture was poured onto crushed ice and the precipitated solid was collected and recrystallized from ethanol (96%, 3 ml) to afford the pure 9-aryl-1,8-dioxo-octhydroxanthenes derivatives (2). Under the same conditions, this approach can be repeated for synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes, 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-1,6,10-ones, 14-aryl-14H-dibenzo[a,i]xanthenes-8,13-ones, 13-aryl-5H-dibenzo[b,i]xanthenes-5,7,12,14 (13H)-tetraones and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones.
82%	With zinc(II) oxide; In neat (no solvent); at 80℃; for 0.583333h;	General procedure: A mixture of 5,5-dimethyl-1,3-cyclohexanedione (0.28 g, 2 mmol), various aldehydes (1 mmol) and ZnO NPs (0.01 g, 0.1 mmol, 10 mol%) was heated at 80 8C for 15-35 min. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and solid obtained was dissolved in dichloromethane, the catalyst was insoluble in CH2Cl2 and separated by a simple filtration. The solvent was evaporated and the residue was recrystallized from ethanol to afford the pure 1,8-dioxooctahydroxanthenes.

Reference： [1]Acta Chimica Slovenica,2016,vol. 63,p. 602 - 608
[2]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2016,vol. 46,p. 151 - 157
[3]RSC Advances,2016,vol. 6,p. 113844 - 113858
[4]Catalysis Communications,2017,vol. 97,p. 138 - 145
[5]Australian Journal of Chemistry,2008,vol. 61,p. 77 - 79
[6]Dyes and Pigments,2015,vol. 123,p. 222 - 234
[7]Chemical Papers,2013,vol. 67,p. 145 - 154
[8]Organic Preparations and Procedures International,2013,vol. 45,p. 220 - 226
[9]Chemistry of Heterocyclic Compounds,2014,vol. 49,p. 1715 - 1722
Khim. Geterotsikl. Soedin.,2013,vol. 49,p. 1852 - 1859,8
[10]Asian Journal of Chemistry,2014,vol. 26,p. 4594 - 4598
[11]Chinese Chemical Letters,2012,vol. 23,p. 1225 - 1229,5
[12]South African Journal of Chemistry,2012,vol. 65,p. 191 - 195
[13]Synthetic Communications,2012,vol. 42,p. 2876 - 2884
[14]Justus Liebigs Annalen der Chemie,1899,vol. 309,p. 380

3
[ 2583-25-7 ]
[ 122-03-2 ]
[ 98590-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; pyridine

Reference： [1]Gensler; Berman [Journal of the American Chemical Society, 1958, vol. 80, p. 4949,4952]

4
[ 939-83-3 ]
[ 122-03-2 ]
4'-isopropyl-4-nitro-stilbene-2-carbonitrile [ No CAS ]

Reference： [1]Chemische Berichte,1918,vol. 51,p. 561

5
[ 939-79-7 ]
[ 122-03-2 ]
4'-isopropyl-2-nitro-stilbene-4-carbonitrile [ No CAS ]

Reference： [1]Chemische Berichte,1918,vol. 51,p. 561

6
[ 64113-86-6 ]
[ 122-03-2 ]
4'-isopropyl-4-nitro-stilbene-3-carbonitrile [ No CAS ]

Reference： [1]Chemische Berichte,1918,vol. 51,p. 561

7
[ 404-90-0 ]
[ 122-03-2 ]
[ 580-80-3 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 193,195

8
[ 1071-36-9 ]
[ 122-03-2 ]
[ 25554-21-6 ]

Reference： [1]Canadian Journal of Research, Section B: Chemical Sciences,1945,vol. 23,p. 84,85

9
[ 122-03-2 ]
[ 536-66-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen; In acetonitrile; at 20℃;Irradiation; Sealed tube; Green chemistry;	General procedure: An oven-dried resealable test tube equipped with a magnetic stir bar was charged withaldehyde (1.0 mmol), Ir(dFppy)3 (0.005-0.01 mmol), and MeCN (4.0 mL, 0.25 M). Oxygen wasthen bubbled through the reaction mixture and sealed with a silicone septa screw-cap. A balloonfilled with oxygen was attached to the tube, and the test tube was placed under blue LEDs atroom temperature. The reaction was allowed to proceed for 3-12 h, and reaction progress waschecked by TLC. The solvent was removed under vacuum, and the corresponding carboxylic acidwas purified by flash silica gel chromatography.
93%	With sodium hydroxide; In water; at 20 - 75℃; for 18h;	General procedure: In a two-necked round bottom flask equipped with a condenser, the aldehyde (1 mmol), was dropped into the mixture of catalyst (4 mol%) and NaOH (1.5 mmol) in deionized water (3 mL). The resulting mixture was stirred at room temperature under air atmosphere for 15 min and then the temperature reached 75 C. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered off and the catalyst rinsed with deionized water and ethanol. The filtrate was treated with H2SO4 (30 wt.%). The precipitated carboxylic acid was filtered, washed with water and dried in vacuum. (For liquid products after addition of H2SO4, the product was extracted using diethyl ether (4 × 5 mL).
87%	With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,4-diaza-bicyclo[2.2.2]octane; oxygen; In tetrahydrofuran; at 20℃; for 16h;	General procedure: To a dry, two-neck 25 mL round-bottom flask equipped with a magnetic stir bar was added NHC catalyst F (0.025 mmol) and aldehyde 1 (0.5 mmol). The reaction vessel was charged with anhydrous THF (3 mL), followed by flushing with O2 gas. DABCO (0.25 mmol) was added and the flask was again flushed with O2 gas. The reaction mixture was stirred for 16 h at r.t. under an O2 atmosphere (1 atm, O2 balloon). After completion of the reaction, as monitored by TLC, the mixture was diluted with EtOAc (10 mL) and aqueous 1.0 M NaOH solution was added. The aqueous layer was separated, washed with EtOAc (10 mL) and acidified using 3.0 M aqueous HCl solution (10 ml). This aqueous layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the pure desired product.

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3867 - 3871
 Angew. Chem.,2017,vol. 129,p. 3925 - 3929,5
[2]ChemCatChem,2018,vol. 10,p. 1253 - 1257
[3]Tetrahedron Letters,2013,vol. 54,p. 6222 - 6225
[4]Tetrahedron Letters,2007,vol. 48,p. 3835 - 3839
[5]Catalysis Communications,2016,vol. 79,p. 26 - 30
[6]Synthesis,2018,vol. 50,p. 4290 - 4294
[7]Chemical Communications,2005,p. 4042 - 4044
[8]Molecules,2020,vol. 25
[9]Annales de Chimie (Cachan, France),1841,vol. <3> 1,p. 68
 Justus Liebigs Annalen der Chemie,1841,vol. 38,p. 74
[10]Journal of the Chemical Society,1938,p. 1408,1413
[11]Journal of the Chemical Society,1940,p. 808
[12]Justus Liebigs Annalen der Chemie,1883,vol. 219,p. 241
[13]Annales de Chimie (Cachan, France),1841,vol. <3> 1,p. 68
 Justus Liebigs Annalen der Chemie,1841,vol. 38,p. 74
[14]Justus Liebigs Annalen der Chemie,1883,vol. 219,p. 241
[15]Justus Liebigs Annalen der Chemie,1883,vol. 219,p. 241
[16]ChemSusChem,2016,vol. 9,p. 3102 - 3112
[17]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3292 - 3298

10
[ 122-03-2 ]
[ 4395-73-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1954,p. 615,617
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6197 - 6208

11
[ 122-03-2 ]
[ 4395-73-7 ]
[ 536-60-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1954,p. 615,617

12
[ 6683-92-7 ]
[ 122-03-2 ]
[ 16736-18-8 ]

Reference： [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1967,vol. 300,p. 748 - 757

13
[ 288-16-4 ]
[ 122-03-2 ]
[ 90672-88-1 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1245 - 1253

14
[ 10557-85-4 ]
[ 122-03-2 ]
[ 90672-49-4 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1245 - 1253

15
[ 13438-65-8 ]
[ 122-03-2 ]
[ 79973-92-5 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 98 - 102

16
[ 16357-40-7 ]
[ 122-03-2 ]
[ 72739-40-3 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 335 - 338

17
[ 3068-00-6 ]
[ 122-03-2 ]
4-hydroxymethyl-2-(4-isopropylphenyl)-1,3-dioxane [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1993,vol. 4,p. 845 - 864

18
[ 141-82-2 ]
[ 122-03-2 ]
[ 117391-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In ethanol; at 78.0℃;	General procedure: Benzaldehyde (1 equiv), propanedioic acid (2 equiv) and ammonium acetate (2 equiv) were added to the solution of anhydrous ethanol (30 mL) and heated to 78 C for 17 h. A lot of precipitated solid was filtered and dried in vacuo at 40 C for 24 h to give a light white solid.

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 9152 - 9157
[2]Bulletin de la Societe Chimique de France,1987,p. 1079 - 1083
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 1356 - 1365

19
[ 111-74-0 ]
[ 122-03-2 ]
N,N'-Diethyl-N-(4-isopropyl-benzyl)-ethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane for 8h; Ambient temperature;

Reference： [1]Watanabe, Toshihiro; Kakefuda, Akio; Kinoyama, Isao; Takizawa, Kenji; Hirano, Seiko; Shibata, Hiroshi; Yanagisawa, Isao [Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 9, p. 1458 - 1469]

20
[ 4395-73-7 ]
[ 122-03-2 ]
(4-Isopropyl-benzyl)-[1-(4-isopropyl-phenyl)-meth-(E)-ylidene]-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 2297 - 2307

21
[ 7647-01-0 ]
anilino-phenyl-acetic acid-(4-isopropyl-benzylidenamide) [ No CAS ]
[ 7664-41-7 ]
[ 3684-12-6 ]
[ 122-03-2 ]

Reference： [1]Chemische Berichte,1898,vol. 31,p. 2702,2703

22
[ 16588-24-2 ]
[ 100-39-0 ]
[ 122-03-2 ]
1-benzyl-6-bromo-2-(4-isopropyl-phenyl)-1H-benzoimidazole [ No CAS ]

Reference： [1]Organic letters,2001,vol. 3,p. 83 - 86

23
[ 68827-43-0 ]
[ 122-03-2 ]
2-(4-isopropyl-phenyl)-3H-benzoimidazole-5-carboxamidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1545 - 1548

24
[ 122-03-2 ]
[ 3717-17-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In methanol; for 24h;Reflux;	4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10% SE-30 on Chromosorb, 10' × 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97%).
95%		General procedure: Scheme 4 illustrates the synthetic procedure for the oximes employed in this work. Their preparation was performed as follows: a microwave vial equipped with a magnetic stirrer was charged with 1mmol of carbonyl compound, 2mmol of hydroxylamine hydrochloride and 1.5mL of 50% v/v water/ethanol. The system was sealed and stirred for 60sat room temperature. Then the vial was irradiated at 120C with automatic power control for 1h. After completion of reaction, the solid products were filtered off and washed with cold water. If desired, the solids may be recrystallized from ethanol-water mixtures, but they usually are very pure compounds, as checked by TLC and GC. If no solid was formed, extraction with ethyl acetate (15mL) and washing of organic layer with water (2 x 15mL) were performed. The organic layer was collected, dried over anhydrous sodium sulphate, filtered and concentrated in the rotary evaporator to give oily products in high purity, in accordance to TLC and GC methods. If desired, oily products may be subjected to flash chromatography, using 10-40% ethyl acetate/hexane mixture. Table 1 depicts all synthesized compounds, yields and relevant estimated physicochemical properties. Spectroscopic data for all synthesized compounds are provided in Supplementary Material.
	With hydroxylamine hydrochloride; In ethanol; at 20℃; for 1h;	To a solution of compound 1-Im-l l (14.8 g, 1.0 eq) in 148 mL of EtOH, hydroxy lamine hydrochloride (1.0 eq) was added. The reaction mixture was stirred at rt for 1 h and concentrated to give compound 2-Im- 11.

	With hydroxyammonium sulfate; In 2,2,2-trifluoroethanol; water; at 20℃; for 1h;	General procedure: One-Pot Synthesis of Isoxazolines 3; General ProcedureTo a mixture of TFE (2.2 mL) and H2O (0.8 mL), an aldehyde 1 (0.5mmol) and hydroxylamine sulfate (0.3 mmol) were first added, andthe mixture was stirred at r.t. for 1 h. Then, m-CPBA (0.7 mmol) andPhI (0.1 mmol) were added and stirring was continued. After 30min, an alkene 2 (1 mmol) was added to the mixture which wasstirred for another 5 h, until the reaction was completed. Then, H2O(10 mL), sat. aq Na2S2O3 (2 mL) and sat. aq Na2CO3 (2 mL) wereadded, and the mixture was stirred for 10 min. The mixture was extractedwith CH2Cl2 (3 × 4 mL) and the combined organic phasewas dried over anhydrous Na2SO4, filtered and concentrated underreduced pressure. The residue was purified by TLC on a silica gelplate (petroleum ether-EtOAc, 3:1) to provide the correspondingpure isoxazoline 3.
	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; at 0 - 20℃;	General procedure: 10 mmol of aldehyde was dissolved in 10 mL of H2O/EtOH(v/v) 1/1) mixture by stirring in a 100-mL round-bottomedflask. The solution was cooled to 0 C, and 10 mmol of hydroxylamine hydrochloride was added to this solution.Then 25 mmol of NaOH as a 50% solution in water was added dropwise. The reaction mixture is allowed to warm slowly to room temperature and stirred for 1 h. The solution was extracted with chloroform, and the aqueous phase was acidified to pH 6 by adding concentrated HCl while keeping the temperature below 30 C and extracted with chloroformto give the oxime products in 90-97% yield. For chlorination of oxime, 1.8 mmol of N-chlorosuccinimide (NCS) was added in one portion to a solution of 10 mmol of oxime in DMF (10 mL). A slight increase in the reaction temperature shows the beginning of the reaction. A small amount of HClgas can be bubbled through the solution when the reaction does not start. In the case of the electron-deficient oximes for starting the reaction, the mixture is heated to 45 C. Theremaining 8.2 mmol of NCS was added in small portions while keeping the temperature below 35 C (below 60 C for electron-deficient oximes). The mixture was then stirredat room temperature for 1 h and quenched with water and extracted with chloroform (3 × 10 mL) to give the imidoyl chloride products in 72-93% yield.
	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; at 20℃; for 3h;	General procedure: Dissolve hydroxylamine hydrochloride (0.21g, 3mmol) in water (6mL) and neutralized with aqueous sodium hydroxide solution (10%). A solution of according aldehyde 11 (2.8mmol) in ethanol (2mL) was slowly added to the above mixture with stirring at room temperature, and stirred for about 3h. upon the completion of reaction, the residue was diluted with ethyl acetate (30mL), and then washed with brine. The organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated in vacuum. The oxime was used without further purification.
		General procedure: To a solution of aromatic aldehyde (10 mmol) in 10 mL of ethanol, 10 mL of an aqueous solution of hydroxylamine hydrochloride (834 mg, 12 mmol) is added, the reaction is stirred for 5 minutes, and then neutralized to pH of 7 by a sodium carbonate solution to precipitate an aromatic aldehyde oxime, which is filtered and dried, and can be used directly for the next reaction. Aromatic aldehyde oxime (1.1 mmol), NCS (161 mg, 1.2 mmol), are added into 10 mL DMF and reacts for 10 minutes at 60 , then 4-alkynyl sinomenine (367 mg, 1 mmol) is added, and Et 3 N in 10 mL DMF is added dropwise in 30 minutes to give 1.3-dipole 7 in situ, the reaction of 7 and 4-alkynyl sinomenine produces sinomenine isoxazole 8. After being concentrated by evaporation in vacuo, 30 mL dichloromethane is added, the dichloromethane is then washed with water (15 mL x 3), dried over anhydrous sodium sulfate, and rotary evaporated to give crude product, purified by column chromatography (CH 2 Cl 2 /CH 3 OH/NH 3 ·H 2 O, 200:10:1-400:10:1, v/v) for characterization.

Reference： [1]Organic Letters,2016,vol. 18,p. 292 - 295
[2]Tetrahedron Asymmetry,2008,vol. 19,p. 921 - 931
[3]Tetrahedron Letters,2012,vol. 53,p. 3421 - 3424
[4]Chemico-Biological Interactions,2019,vol. 309
[5]Journal of Organic Chemistry,2013,vol. 78,p. 8386 - 8395
[6]Synthetic Communications,2001,vol. 31,p. 3151 - 3159
[7]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1126 - 1128
[8]Monatshefte fur Chemie,2010,vol. 141,p. 461 - 469
[9]Patent: WO2011/79114,2011,A1 .Location in patent: Page/Page column 110
[10]Synthesis,2014,vol. 46,p. 503 - 509
[11]Advanced Synthesis and Catalysis,2016,vol. 358,p. 774 - 783
[12]European Journal of Organic Chemistry,2018,vol. 2018,p. 506 - 514
[13]Journal of the Iranian Chemical Society,2018,vol. 15,p. 813 - 821
[14]Applied Organometallic Chemistry,2018,vol. 32
[15]European Journal of Medicinal Chemistry,2018,vol. 159,p. 90 - 103
[16]New Journal of Chemistry,2019,vol. 43,p. 709 - 717
[17]Organic Letters,2019,vol. 21,p. 2134 - 2138
[18]Natural Product Research,2019

25
[ 3717-17-7 ]
[ 122-03-2 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 22918 - 22921
[2]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1761 - 1764

26
[ 87120-72-7 ]
[ 73152-70-2 ]
[ 122-03-2 ]
[ 10111-08-7 ]
4-pentyl-bicyclo[2.2.2]octane-1-carboxylic acid [1-(1H-imidazol-2-ylmethyl)-piperidin-4-yl]-(4-isopropyl-benzyl)-amide [ No CAS ]

Reference： [1]Molecules,2003,vol. 8,p. 556 - 564

27
[ 650-51-1 ]
[ 122-03-2 ]
[ 55011-04-6 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 4449 - 4452

28
[ 5267-34-5 ]
[ 122-03-2 ]
[ 840500-43-8 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 1691 - 1709

29
[ 122-03-2 ]
[ 76-05-1 ]
[ 177911-87-4 ]
C-[1-(4-isopropyl-benzyl)-pyrrolidin-2-yl]-methylamine; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2723 - 2737

30
[ 122-03-2 ]
[ 76-05-1 ]
[ 162167-97-7 ]
C-[1-(4-isopropyl-benzyl)-piperidin-3-yl]-methylamine; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2723 - 2737

31
[ 1078-28-0 ]
[ 141-43-5 ]
[ 122-03-2 ]
1-(2-Amino-ethyl)-2-[(E)-2-(4-isopropyl-phenyl)-vinyl]-6-methoxy-quinolinium [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 6331 - 6335

32
[ 105-45-3 ]
[ 17356-08-0 ]
[ 122-03-2 ]
4-(4-isopropyl-phenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With Fe3O4(at)SiO2(at)Me&Et-PhSO3H; In neat (no solvent); at 100℃; for 2h;Green chemistry;	General procedure: A mixture of aldehyde (2mmol), methyl acetoacetate (2mmol), urea/thiourea (2.4mmol) and catalyst 2 (7.1mg, 0.5mol %) (in the case of thiourea, 1mol % of the catalyst was used) was stirred at 100C for an appropriate time under solvent-free condition (Table 3). The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was washed with water (3× 10mL). Finally, the mixture was dissolved in hot EtOH and the catalyst was separated by magnetic decantation. The crude product was either recrystallized from EtOH or subjected to preparative thin layer chromatography (silica gel) for further purification.
88%	With 1-butyl-1,2,4-triazolium triflate; In ethanol; at 80℃; for 2.3h;Green chemistry;	General procedure: Catalyst 1a-c (10 mol%) was added to a solution of aldehyde (1.0 mmol), beta-ketoester (1.5 mmol) and urea or thiourea (2.0 mmol) in ethanol (0.5 mL). The reaction mixture was heated at 80 C using oil bath for the specified time (0-5 h). The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature and subsequently quenched with a mixture of water:ethanol (5:0.5 mL). The solid product was filtered and washed with n-hexane (5mL ×2), which afforded pure 3,4-dihydropyrimidin-2(1H)-ones or 3,4-dihydropyrimidin-2(1H)-thiones in pure form.
84%	With 1-ethyl-1,2,4-triazolium phenylsulfonate; In ethanol; at 70 - 80℃; for 4.5h;	General procedure: Catalyst 1-ethyl-1,2,4-triazolium phenylsulfonate (TrHEtPS) (10 mol) was added to a solution of urea or thiourea (2.0 mmol), beta-ketoester (1.5 mmol) and aldehyde (1.0 mmol) in ethanol (0.5 mL). The reaction mixture was heated at 70 to 80 C for the specified time (0-5 h) (Scheme-II). The completion of the reaction was monitored by thin layer chromatography (ethyl acetate:hexane: :4:1) and then the reaction mixture was cooled to room temperature. Then, quenched with mixture of water: ethanol (5:0.5 mL). The obtained solid product was filtered, and washed with n-hexane (5mL) and afforded 3,4-dihydropyrimidin-2(1H)-ones or 3,4-dihydropyrimidin-2(1H)-thiones.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 2018 - 2020
[2]ChemCatChem,2014,vol. 6,p. 212 - 219
[3]Applied Catalysis A: General,2014,vol. 472,p. 123 - 133
[4]Journal of Chemical Sciences,2015,vol. 127,p. 1539 - 1545
[5]Asian Journal of Chemistry,2018,vol. 30,p. 1999 - 2002

33
[ 57-71-6 ]
[ 122-03-2 ]
[ 870539-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In acetic acid;	4,5-Dimethyl-2-(4-(2-propyl)-phenyl)-oxazole 3-oxide 18.4 g of diacetyl monoxime and 29.6 g of 4(2-propyl)-benzaldehyde are added to 50 ml of glacial acetic acid, and HCl gas is introduced with ice-cooling for 30 minutes. The product is precipitated as the hydrochloride by addition of methyl tert-butyl ether and filtered off with suction, and the precipitate is washed with methyl tert-butyl ether.

Reference： [1]Patent: US2005/267177,2005,A1

34
[ 122-03-2 ]
[ 23152-99-0 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 1023 - 1027

35
[ 122-03-2 ]
[ 88371-24-8 ]

Reference： [1]Chemische Berichte,1889,vol. 22,p. 2279
Chemische Berichte,1890,vol. 23,p. 3086

36
[ 122-03-2 ]
[ 38628-51-2 ]

Reference： [1]Chemische Berichte,1889,vol. 22,p. 2279
Chemische Berichte,1890,vol. 23,p. 3086

37
[ 56-92-8 ]
[ 122-03-2 ]
[ 303021-39-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium hydroxide; In ethanol; water; for 1.5h;Heating / reflux;	A mixture of histamine dihydrochloride (1.85 g, 10.0 mmol), water (10 mL), potassium hydroxide (1.72 g, 30.0 mmol), ethanol (25 mL) and 4-isopropylbenzaldehyde (1.62 g, 10.91 mmol) was heated to reflux for 1.5 h. Ethanol was evaporated and the residue was diluted with water (40 mL). Extraction (5×25 mL DCM), washing of the combined extracts (2×50 mL brine) and drying (MgSO4) yielded 2.29 g (87%) of crude 4-(4-isopropylphenyl)-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine, which was used for the next synthetic step without further purification. This amine (0.48 g, 1.99 mmol) was dissolved in DCM (5 mL) and added to a 30 min old mixture of 3-(4-fluorophenyl)propionic acid (0.31 g, 1.84 mmol), HOBt (0.27 g, 1.20 mmol) and EDC (0.42 g, 12.19 mmol) in DCM (10 mL). After 18 h the mixture was washed with water (50 mL), dried (MgSO4) and concentrated. The crude product was purified by column chromatography (silica gel, gradient elution with DCM/methanol). 0.24 g (33%) of the title amide was obtained.HPLC (214 nm): elution at 10.21 min. LC-MS: Calcd. for MH+: 392; found: 392.1H NMR (400 MHz, DMSO-d6): delta1.18 (d, J=7 Hz, 6H), 2.50-2.94 (m, 7H), 3.05 (m, 1H), 3.95 (m, 1H), 6.48 (s, br, 0.7H), 6.67 (s, br, 0.3H), 6.99-7.35 (m, 8H), 7.55 (s, 1H), 11.90 (s, 1H).

Reference： [1]Patent: US6908926,2005,B1 .Location in patent: Page/Page column 46

38
[ 81868-12-4 ]
[ 64-19-7 ]
[ 122-03-2 ]
C₂H₄O₂*C₂₀H₂₁BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	for 0.25 - 20h;Heating / reflux;	In one embodiment, Procedure-1 may involve adding a desired Aldehyde (II) to a suspension of 5-substituted tryptamine. HC1 (1) in 0. 1N sulfuric acid. The solution may then be stirred at about 110C-120C in a closed reaction vessel until the reaction is sufficient to complete, e. g., for about 15 minutes to about 20 hours. After completion of the reaction, the reaction mixture may be cooled to room temperature and the precipitated salt may be filtered. The filtered residue may then be washed with ether, EtOAc or a mixture of DCM and DMF and dried to give the product (III) as acid salt. Alternatively, a desired Aldehyde (II) may be added to a suspension of 5-substituted tryptamine. HCl (I) in acetic acid and refluxed until the reaction is sufficiently complete, e. g., for about 15 minutes to about 20 hours. After completion of the reaction, the reaction mixture may be cooled to room temperature and the acid salt may be filtered. The filtered residue may then be washed with acetic acid followed by DCM and dried to give the product (III) as acid salt. The free amine (III) may be obtained by extraction with EtOAc and washing with aqueous ammonium hydroxide or 1M aq. sodium hydroxide.; Intermediate-9 (Compound 112) : This product/intermediate is prepared using Procedure-I with <strong>[81868-12-4]5-bromotryptamine</strong>. HCl (551 mg, 2 mmol), 4-isopropyl benzaldehyde (606 I1L, 4 mmol) and 0. 1N sulfuric acid (8 mL) to give the title compound as hydrogen sulfate salt (329 mg, 35%). ES-MS: 369 (M+H) +. Alternatively, this intermediate is prepared using Procedure-lB with <strong>[81868-12-4]5-bromotryptamine</strong>. HCl (10 g, 36.3 mmol), 4-isopropyl benzaldehyde (8.24 mL, 54.5 mmol) and acetic acid (120 mL) to give the title compound as acetate salt (13 g, 77%). ES-MS: 369 (M+H) +

Reference： [1]Patent: WO2005/89764,2005,A1 .Location in patent: Page/Page column 101-102; 114

39
[ 81868-12-4 ]
[ 122-03-2 ]
C₂₀H₂₁BrN₂*H₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sulfuric acid; In water; at 110 - 120℃; for 0.25 - 20h;	In one embodiment, Procedure-1 may involve adding a desired Aldehyde (II) to a suspension of 5-substituted tryptamine. HC1 (1) in 0. 1N sulfuric acid. The solution may then be stirred at about 110C-120C in a closed reaction vessel until the reaction is sufficient to complete, e. g., for about 15 minutes to about 20 hours. After completion of the reaction, the reaction mixture may be cooled to room temperature and the precipitated salt may be filtered. The filtered residue may then be washed with ether, EtOAc or a mixture of DCM and DMF and dried to give the product (III) as acid salt. Alternatively, a desired Aldehyde (II) may be added to a suspension of 5-substituted tryptamine. HCl (I) in acetic acid and refluxed until the reaction is sufficiently complete, e. g., for about 15 minutes to about 20 hours. After completion of the reaction, the reaction mixture may be cooled to room temperature and the acid salt may be filtered. The filtered residue may then be washed with acetic acid followed by DCM and dried to give the product (III) as acid salt. The free amine (III) may be obtained by extraction with EtOAc and washing with aqueous ammonium hydroxide or 1M aq. sodium hydroxide.; Intermediate-9 (Compound 112) : This product/intermediate is prepared using Procedure-I with <strong>[81868-12-4]5-bromotryptamine</strong>. HCl (551 mg, 2 mmol), 4-isopropyl benzaldehyde (606 I1L, 4 mmol) and 0. 1N sulfuric acid (8 mL) to give the title compound as hydrogen sulfate salt (329 mg, 35%). ES-MS: 369 (M+H) +. Alternatively, this intermediate is prepared using Procedure-lB with <strong>[81868-12-4]5-bromotryptamine</strong>. HCl (10 g, 36.3 mmol), 4-isopropyl benzaldehyde (8.24 mL, 54.5 mmol) and acetic acid (120 mL) to give the title compound as acetate salt (13 g, 77%). ES-MS: 369 (M+H) +

Reference： [1]Patent: WO2005/89764,2005,A1 .Location in patent: Page/Page column 101-102; 114

40
[ 120-35-4 ]
[ 122-03-2 ]
3-(4-Isopropyl-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 243 3-(4-Isopropyl-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-isopropylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 174-176 C.

Reference： [1]Patent: US6268387,2001,B1

41
[ 36768-62-4 ]
[ 80-52-4 ]
[ 13472-00-9 ]
[ 61-54-1 ]
[ 299-26-3 ]
[ 608-07-1 ]
[ 50541-93-0 ]
[ 53369-71-4 ]
[ 6530-09-2 ]
[ 58859-46-4 ]
[ 7144-05-0 ]
[ 122-03-2 ]
3-amino-pyrrolidine dihydrochloride [ No CAS ]
[ 69500-64-7 ]
[ 1019536-85-6 ]
[ 940197-00-2 ]
[ 1036476-02-4 ]
C₁₈H₂₈N₂O₂ [ No CAS ]
[ 892588-71-5 ]
C₂₁H₂₆N₂ [ No CAS ]
[ 940198-38-9 ]
C₂₁H₂₆N₂O [ No CAS ]
C₂₄H₃₄N₂ [ No CAS ]
C₂₅H₃₆N₂ [ No CAS ]
[ 959329-07-8 ]
[ 849909-44-0 ]
C₃₀H₄₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 24 - 36h;Combinatorial reaction / High throughput screening (HTS);	All sixty diamines were separated in four groups based on their steric and electronic characteristics, Figures 1-4. Each diamine was measured in the amount of 0.05 g (approximately 0.3 mmol) and pooled together with the others in the group. Obtained diamine mixtures were dissolved in 5 ml of 1,2-dichloroethane and used for the syntheses. Each well of the 96-well filterplates was loaded with 0.2 ml of 1: 10 mixture of acetic acid: DCE, 0.03 ml of the diamine mixture in DCE (group 1, group 2, group 3, or group 4) to assure 0.04 mmol of the diamines per well, and shaken for 5 min at room temperature. Appropriate carbonyl compounds from the master plate (0.1 ml of 1.2 M solution) were added into corresponding wells of the reaction plates followed by the addition of (polystyrylmethyl) trimethylammonium cyanoborohydride, (0.020 g, 0.08 mmol per well). The reaction plates were sealed and placed on a shaker. The reaction was allowed to proceed 24-36 hours at room temperature. At the end, the reaction mixtures were filtered using a filtration manifold, and products were collected into four (one per group) collection plates. Solvents were evaporated in SpeedVac and formed residues were analyzed by mass spectrometry prior to biological screening. Mono and double alkylated products were observed in 1: 0.5 to 1: 2 ratios by mass spectral analysis.

Reference： [1]Patent: WO2005/34857,2005,A2 .Location in patent: Page/Page column 15; 22

42
[ 3717-17-7 ]
[ 13816-33-6 ]
[ 122-03-2 ]

Reference： [1]Synthesis,2008,p. 1997 - 1999

43
[ 126-81-8 ]
[ 122-03-2 ]
[ 109-77-3 ]
[ 302323-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ethylenediamine functionalized hyper-crosslinked polyphenanthrene; In neat (no solvent); at 20℃;Green chemistry;	General procedure: p-methoxybenzaldehyde 1{11} (1 mmol), MN 2{1} (1 mmol),dimedone 3{1} (1 mmol), and PPhEDA (10 mg) were mixed at r.t.under solvent-free conditions with stirring. The reaction progress was monitored by TLC (hexane:EA = 6:4). When the reaction was complete, EA (8 mL) was added, and the reaction mixture was centrifuged for 30 min at 6000 rpm. The solvent was decanted and concentrated using a rotary evaporator. The crude product was purified by recrystallization from EtOH (10 mL). This procedure was used for all title compounds. In the re-usability tests, PPhEDA was washed with EA (2 × 8 mL) and dried under vacuum at 80C for 1 h.Detailed spectral data for all the compounds, 1H and13C NMR are given in the Supporting Information (SI).
89%	With silica-bonded N-propylpiperazine sodium n-propionate; In ethanol; water; for 0.75h;Reflux;	General procedure: To a mixture of aromatic aldehyde (1 mmol), malonitrile (1mmol), and dimedone (1 mmol) in 3 mL of aqueous ethanol (1:1), SBPPSP catalyst (0.05 g, 4.3 mol%) was added, and the mixture was refluxed for an appropriate time. After completion of the reaction, as indicated by thin-layer chromatography(TLC), ethanol (10 mL) was added, and the reaction mixture was filtered. The residue was washed with warm ethanol (3 × 5 mL) to separate the heterogeneous catalyst. After cooling, the crude product was precipitated and then purified by recrystallization from ethanol (95%). The recovered catalyst was dried and reused in further reactions.
89%	With nickel(II) ferrite; In ethanol; at 40℃; for 0.833333h;Green chemistry;	General procedure: A solution of aldehyde 1a-1y (1 mmol), dimedone 2 (1 mmol), malononitrile 3 (1 mmol), and ethanol (4 mL)was magnetically stirred at room temperature. To the mixture, NiFe2O4 MNPs (5 mol%) were added and the content was heated at 40 C for the appropriate time. The progress of the reaction was checked by TLC(n-hexane:EtOAc, 10:6). After completion, the resulting product was heated in ethanol. The catalyst was magnetically removed from the mixture and washed several times with ethanol for reuse. The pure product was collected from the ltrate after cooling to room temperature with an ice bath and then was recrystallized from hot ethanol.

79%	With L-prolinate anion immobilized onto anion-exchange resin amberlite; In ethanol; for 0.666667h;Reflux;	General procedure: beta-Naphthol or enolizable compound (1 mmol), aldehyde (1 mmol), and malononitrile (1 mmol), were placed together in a round-bottom flask containing 5 mL of EtOH. [Amb]L-prolinate catalyst (0.08 g, 10 mol%) was added to the mixture. The suspension was magnetically stirred at reflux for an appropriate time according to Table 2. After completion of the reaction, as followed by TLC (n-hexane : ethylacetate; 3 : 1), the catalyst was filtered and washed with hot ethanol (2 x 5 mL). The recovered catalyst was washed with acetone, dried, and stored for other similar consecutive runs. The filtrate mixture was recrystallized to provide the pure crystals of 2-amino-4H-chromene derivatives. The products are known compounds and are characterized by IR and NMR spectroscopy data for new compounds. Their melting points are compared with reported values.
62%	With H5[SiW11FeIII(H2O)O39] supported on the surface of aminopropyl-modifed silica-coated magnetite nanoparticle; In neat (no solvent); at 80℃; for 0.333333h;	General procedure: To a mixture of aromatic aldehyde (1.0mmol), malononitrile (1.0mmol), and dimedone (1.0mmol) was added 0.03g H5SiW11Fe-APSCMNPs. Then, the mixture was stirred at 80 C in an oil bath under solvent-free condition for appropriate time. After reaction completion as monitored by TLC, the mass was cooled to 25C, and the mixture was dissolved in boiling ethanol; fnally, catalyst was separated using an external magnet. Afterward, the liquor was poured into ice. The mixture was fltered to separate the product. The crude product was purifed by recrystallization from ethanol to obtain pure tetrahydrobenzo[b]pyran derivatives. The purity of the products was determined by comparison of their physical data, viz. melting point, FT-IR, and 1 H and 13C nuclear magnetic resonance (NMR) spectra, with known compounds in literature [36-38].
	With dmap; In ethanol;Reflux;	General procedure: Dihydropyran derivatives (5-8) were also synthesized accordingto a reported procedure (Eshghi et al. 2012). Amixtureof 3,5-cyclohexanedione (or 1,1-dimethyl-3,5-cyclohexanedione)(10 mmol), 4-methylsulfanylbenzaldehyde (or 4-nitrobenzaldehyde,4-isopropylbenzaldehyde, 3-bromo-4-fluorobenzaldehyde) (10 mmol),malononitrile (10 mmol) and4-(dimethylamino)pyridine (DMAP) (1 mmol) in ethanol(100 mL) was refluxed for 2-3 h and then cooled to roomtemperature. After filtering the precipitates, they were sequentiallywashed with ice-cooled water and ethanol and thendried under a vacuum. 2-Amino-4-(4-methylsulfanylphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (5): m.p. 224-225 C. IR (KBr pellet cm-1): 1681 (CO), 1651 (C=C),1214 (-O-). 1H NMR (DMSO-d6, delta, ppm): 7.169-7.190(t, 2H), 7.087-7.107 (d, 2H), 7.029 (s, 2H), 4.149 (s, 1H),2.590-2.621 (q, 2H), 2.499-2.516 (m, 3H), 2.216-2.311(m, 2H), 1.864-1.981 (m, 2H). HRMS (ESI+): m/z: calcdfor [C17H16N2O2S?Na+]: 335.0825; found: 335.0832.

Reference： [1]Applied Catalysis A: General,2017,vol. 538,p. 9 - 18
[2]Synlett,2011,p. 791 - 796
[3]Applied Organometallic Chemistry,2020
[4]Comptes Rendus Chimie,2011,vol. 14,p. 878 - 882
[5]Green Chemistry,2012,vol. 14,p. 1696 - 1704
[6]Journal of the Chinese Chemical Society,2020,vol. 67,p. 1120 - 1131
[7]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 2245 - 2254
[8]Turkish Journal of Chemistry,2018,vol. 42,p. 719 - 734
[9]RSC Advances,2014,vol. 4,p. 9509 - 9516
[10]New Journal of Chemistry,2015,vol. 39,p. 4452 - 4463
[11],2020
[12]Synthetic Communications,2009,vol. 39,p. 433 - 442
[13]Applied Organometallic Chemistry,2018,vol. 32
[14]Research on Chemical Intermediates,2016,vol. 42,p. 4591 - 4604
[15]Research on Chemical Intermediates,2018,vol. 44,p. 2195 - 2213
[16]Archives of Pharmacal Research,2016,vol. 39,p. 1349 - 1355

44
[ 4476-28-2 ]
[ 477219-29-7 ]
[ 122-03-2 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 3321 - 3324

45
[ 1076-38-6 ]
[ 122-03-2 ]
[ 109-77-3 ]
[ 326919-60-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica-supported molybdic acid (SSMA); In ethanol; water; for 0.75h;Reflux;	General procedure: Malononitrile (3, 1.1 mmol), aromatic aldehyde 4(1 mmol), 4-hydroxycoumarin (5, 1 mmol), and SSMA (2,5 mol%) were added to a 10-cm3 mixture EtOH/H2O (50/50) in a 25-cm3 Pyrex flask and refluxed for an appropriatetime (Table 3). The reaction progress was controlled bythin layer chromatography (TLC) using hexane/EtOAc(1:1). After completion of the reaction, the solvent wasremoved under vacuum, the crude products 6 wereobtained after recrystallization from EtOH.
92%	With molybdic acid functionalized silica based Fe3O4 nanoparticles; In ethanol; water; for 0.666667h;Reflux;	General procedure: Malononitrile 4 (1.1 mmol), aromatic aldehyde 5 (1mmol), 4-hydroxycoumarin 6 (1 mmol), and nano-Fe3O4(at)SiO2-OMoO3H (0.02 g) were added to a 10 mL mixture EtOH/H2O (50/50) in a 25-mL pyrex flask and refluxed for an appropriate time (Table 3). The reaction progress was controlled by thin layer chromatography(TLC) using hexane/EtOAc (1:1). After completion of the reaction, the solvent was removed under vacuum, the crude products 7 were obtained after recrystalization from EtOH.
91%	With 4,4'-trimethylene-N,N'-sulfonic acid dipiperidinium chloride; In neat (no solvent); at 20℃; for 0.5h;Milling;	General procedure: The aldehyde (1.0 mmol), malononitrile (1.0 mmol), active methylene compounds (1.0 mmol) [hydroxy-6-methyl-2-pyrone (A), 4-hydroxycoumarin (B) or dimedone (C)], TMDPS (5mol%) were ground vigorously using the planetary ball mill at room temperature for 30 min. The progress of the reaction was monitored by TLC. On completion of the reaction, the product was extracted by hot ethyl acetate which after evaporation of the solvent, the solid crude product was purified just by recrystallization from ethanol without tedious column chromatographic purification. The TMDPS was concentrated under reduced pressure, and the reaction jarwas recharged with new reactants for another reaction. The structure of each purified 4H-pyran-annulated heterocyclic scaffolds was confirmed by melting point and spectral studies including FT-IR, 1H NMR, 13C NMR, and elemental analysis. All the known compounds had physical and spectroscopic data identical to the literature data

88%	With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2; In ethanol; water; at 20℃; for 0.25h;Sonication;	General procedure: To a mixture of an aldehyde (1 mmol), an appropriate C-H acid 3, 5, or 7 (1 mmol) and malononitrile (1.1 mmol) in 6 mL of ethanol:water (2:1) was added Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 (8 mg), and it was sonicated at ambient temperature. After completion of the reaction (TLC), the catalyst was separated from the mixture by an external magnet and washed and dried for subsequent uses. The obtained solid precipitate was filtered and recrystallized from ethanol to afford the corresponding pure pyran derivatives.
84%	With Nanomagnetic bisferrocene-containing ionic liquid supported on silica coated Fe3O4; In neat (no solvent); at 100℃; for 0.483333h;	General procedure: A mixture of aldehyde (1 mmol), 4-hydroxycoumarin (1 mmol),malononitrile (1.1 mmol) and 0.006 g of Fe3O4SiO2(at)imidazolbisFc[HCO3] nanocatalyst was heated at 100 C under solvent-freecondition. After completion of the reaction follow by TLC (n-hexane:ethyl acetate; 6:4) the catalystwas separated using an externalmagnet and the reaction mixture was cooled and the precipitatewas filtered. The crude product was crystallized from ethanol. Thestructures of all the new products were confirmed by FT-IR, 1HNMR, 13C NMR and CHNS analyses.
83%	With L-prolinate anion immobilized onto anion-exchange resin amberlite; In ethanol; for 0.666667h;Reflux;	General procedure: beta-Naphthol or enolizable compound (1 mmol), aldehyde (1 mmol), and malononitrile (1 mmol), were placed together in a round-bottom flask containing 5 mL of EtOH. [Amb]L-prolinate catalyst (0.08 g, 10 mol%) was added to the mixture. The suspension was magnetically stirred at reflux for an appropriate time according to Table 2. After completion of the reaction, as followed by TLC (n-hexane : ethylacetate; 3 : 1), the catalyst was filtered and washed with hot ethanol (2 x 5 mL). The recovered catalyst was washed with acetone, dried, and stored for other similar consecutive runs. The filtrate mixture was recrystallized to provide the pure crystals of 2-amino-4H-chromene derivatives. The products are known compounds and are characterized by IR and NMR spectroscopy data for new compounds. Their melting points are compared with reported values.
	With dmap; In ethanol;Reflux;	General procedure: Dihydropyran derivatives (5-16) were also synthesized according to a reported procedure. A mixture of 4-hydroxycoumarin (1,1-dimethyl-3,5-cyclohexanedione, or 1,3-cyclopentadione) (10 mmol), aromatic aldehydes (10 mmol), malononitrile (10 mmol) and 4-(dimethylamino)pyridine (DMAP) (1mmol) in ethanol (100mL) was refluxed for 2-3 h and then cooled to room temperature. After filtering the precipitates, they were sequentially washed with ice-cooled water and ethanol and then dried under a vacuum.

Reference： [1]Monatshefte fur Chemie,2016,vol. 147,p. 1117 - 1124
[2]New Journal of Chemistry,2015,vol. 39,p. 8576 - 8581
[3]Acta Chimica Slovenica,2017,vol. 64,p. 707 - 713
[4]Tetrahedron Letters,2009,vol. 50,p. 4125 - 4127
[5]Journal of Molecular Liquids,2019,vol. 277,p. 794 - 804
[6]Research on Chemical Intermediates,2019,vol. 45,p. 1841 - 1862
[7]RSC Advances,2017,vol. 7,p. 46644 - 46650
[8]Journal of Organometallic Chemistry,2018,vol. 870,p. 38 - 50
[9]Tetrahedron,2010,vol. 66,p. 5637 - 5641
[10]Research on Chemical Intermediates,2016,vol. 42,p. 4591 - 4604
[11]New Journal of Chemistry,2015,vol. 39,p. 4452 - 4463
[12]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 3876 - 3880

46
[ 28785-06-0 ]
[ 122-03-2 ]
[ 1186022-33-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5632 - 5638

47
[ 119072-55-8 ]
[ 122-03-2 ]
[ 17220-38-1 ]
[ 1224473-86-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 1525 - 1543

48
[ 88333-03-3 ]
[ 122-03-2 ]
[ 17220-38-1 ]
[ 1224473-88-4 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 1525 - 1543

49
[ 2899-28-7 ]
[ 122-03-2 ]
[ 1227610-55-0 ]
[ 1227610-54-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3587 - 3599

50
[ 1445-69-8 ]
[ 126-81-8 ]
[ 122-03-2 ]
[ 1245471-24-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With beta?cyclodextrin sulfonic acid; In neat (no solvent); at 80℃; for 0.166667h;Green chemistry;	General procedure: A mixture of phthalhydrazide (1.0 mmol), aldehyde (1 mmol), 5,5-dimethyl-1,3-cyclohexanedione or 1,3-cyclohexanedione (1.0 mmol),beta -cyclodextrin-SO3H (10 mol %) was heated at 80 C under solvent free condition for an appropriate time as mentioned in Table 1. After completion of the reaction as monitored by TLC the reaction mixture was allowed to cool to room temperature and the residue was diluted with water. The precipitate formed was collected by filtration at pump,washed with water, and dried. The residue recrystallized from ethanol to afford the pure product of 2H-indazolo[2,1-b]phthalazine-trione derivatives. 3,3-Dimethyl-13-phenyl-3,4-dihydro-1H-indazolo[1,2-b]phthalazine-1,6,11(2H,13H)-trione (1) Yellow powder, mp: 200-202 C; 1H NMR (400 MHz, CDCl3) d (ppm)1.23 (s, 6H, -(CH3)2), 2.35 (s, 2H, -CH2-C=), 3.26 and 3.41 (2H, AB system,J = 16 Hz, CHaHbCO), 6.47 (s,1H, -CH-N), 7.61 (d, J = 8 Hz, 2H, Ar-H),7.90-7.85 (m, 2H, Ar-H), 8.37-8.16 (m, 5H, Ar-H); 13C NMR (CDCl3, 100 MHz)d (ppm) 28.5 (-CH3), 28.7 (-CH3), 34.7 (-C(CH3)2), 38.1 (-CH2-C=), 50.9(-CH2CO), 64.9 (-CH-N), 118.6 (-HC-C-CO-), 127.1 (Ar-C), 127.7 (Ar-C),127.9 (Ar-C), 128.7 (Ar-C), 128.9 (Ar-C), 129.1 (Ar-C), 133.6 (Ar-C), 134.5(Ar-C), 136.4(-N-C-CH2-), 150.9 (Ar-C), 154.3 (-N-CO-), 156.1 (-N-CO-),192.2 (-CO-); HRMS m/z calcd for C23H20N2O3 [M?] 372.4165, found 372.4167.
91%	With silica-supported tungstic acid; In neat (no solvent); at 80℃; for 0.55h;Green chemistry;	General procedure: A mixture of phthalhydrazide (1, 1 mmol), 4-chlorobenzaldehydes (2, 1 mmol), dimedone (3, 1 mmol) and silica-supported tungstic acid (STA 10 mol%) was stirred at 80 C under solvent-free conditions. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was washed with ethanol. The residue dissolved in DCM, and the insoluble STA was separated by simple filtration and washed with DCM. The solvent was evaporated under reduced pressure and the obtained crude was recrystallized from ethanol to afford the pure yellow product 4a. The recovered catalyst was washed with ethanol and acetone, dried and reused. Compounds 4a-4w were also synthesized by adopting this procedure.
87%	With 1-sulfonic acid-3,5,7-trimethylpurinium-5,7-dione hydrogen sulfate; In neat (no solvent); at 100℃; for 0.666667h;Green chemistry;	General procedure: A mixture of dimedone (0.035 g, 0.25 mmol), phthalhydrazide (0.040 g, 0.25 mmol), benzaldehyde (0.026 g, 1 mmol), and 3-sulfonic acid imidazopyridinium hydrogen sulfate (10 mmol) was heated at 100C for 10 min. After cooling, the residue was re-crystallized from ethanol to afford the corresponding pure product.

86%	With yttrium(III) trifluoromethanesulfonate; In ethanol; water; at 80℃; for 0.5h;Green chemistry;	General procedure: A mixture of 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione (1,3-dicarbonyl compounds) 1 (2 mmol) with p-substituted benzaldehyde 2 (2 mmol), phthalhydrazide 3 (2 mmol), and 20 mol % of Y(OTf)3 in 10 mL of EtOH-H2O (1 : 1, v/v) was stirred magnetically upon refluxing till completion of the reaction (monitored by TLC) (Table 1). The raw product was filtered off, washed with water and crystallized from EtOH to give the corresponding pure product 4a-4e.
85%	With Fe3O4-SiO2 core-shell nanoparticles; at 120℃; for 0.333333h;Green chemistry;	General procedure: A mixture of dimedone (0.14 g, 1 mmol), phthalhydrazide (0.16 g, 1 mmol), aldehyde (1 mmol), and Fe3O4 SiO2 (0.0 23 gr, 0.8 mmol, 8 mol%) was heated at 120C for 10-20 min. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and the solid obtained was dissolved in dichloromethane; the catalyst was insoluble in CH2Cl2 and separated by using an external magnet. The solvent was evaporated and the residue was recrystallized from ethanol to afford the pure indazolo[1,2-b]-phthalazinetriones.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 1707 - 1728
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 201 - 210
[3]Helvetica Chimica Acta,2010,vol. 93,p. 1375 - 1380
[4]Journal of Molecular Liquids,2015,vol. 206,p. 119 - 128
[5]Russian Journal of Organic Chemistry,2019,vol. 55,p. 250 - 253
[6]Research on Chemical Intermediates,2015,vol. 41,p. 7703 - 7714

51
[ 1122-91-4 ]
[ 77047-87-1 ]
[ 28785-06-0 ]
[ 122-03-2 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 5181 - 5183

52
[ 122-03-2 ]
[ 79878-27-6 ]
[ 1207382-93-1 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 3056 - 3061

53
[ 1544-85-0 ]
[ 762-04-9 ]
[ 122-03-2 ]
[ 1334047-69-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With silica-supported boron trifluoride; at 20℃; for 0.1h;Ionic liquid;	General procedure: A mixture of p-methoxybenzaldehyde (2f, 1 mmol), 5-amino 2,2-difluoro-1,3-benzodioxole (1, 1 mmol), diethyl phosphite (3, 1 mmol), and BF3·SiO2 (5 mol %) were taken in a 10-mL round-bottomed flask containing 1 mL of ([bmim][HCl]) was stirred at room temperature for 5 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated, and the crude product was recrystallized from iso-propanol, and chloroform (85:15) to afford pure alpha-aminophosphonates in 97% yield. This procedure was applied successfully for the preparation of other compounds (Table 1).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 4764 - 4767

54
[ 5425-44-5 ]
[ 122-03-2 ]
[ 1333394-40-3 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: Compound 4a (510 mg, 2.12 mmol) was dissolved in 5 mL of anhydrous THF and n-BuLi (1.39 mL, 2.22 mmol) was added drop wise. The mixture was stirred at -78 C under argon during 1 h and then benzaldehyde (280 muL, 2.75 mmol) was added. The reaction was left to warm to room temperature and stirred for 5 h. The reaction was quenched by the addition of NH4Cl 0.5 M (5 mL) and the organic phase was collected and dried over Na2SO4. The solution was filtered and the solvent evaporated. The product was purified by column chromatography (SiO2, CH2Cl2), to afford (R,S)-5d as a white solid (550 mg. 1.59 mmol, 75% yield).

Reference： [1]Tetrahedron,2011,vol. 67,p. 7321 - 7329

55
[ 118-93-4 ]
[ 122-03-2 ]
[ 92831-11-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 20 °C 2: copper(l) iodide; oxygen / 48 h / 50 °C / 760.05 Torr / Ionic liquid

Reference： [1]Du, Zhiyun; Ng, Huifen; Zhang, Kun; Zeng, Huaqiang; Wang, Jian [Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 6930 - 6933]

56
[ 122-03-2 ]
[ 213971-37-0 ]
[ 1353852-04-6 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 373 - 376

57
[ 141-97-9 ]
[ 126-81-8 ]
[ 122-03-2 ]
[ 379247-27-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium acetate; 2-methylpyridinium trifluoromethanesulphonate; In water; at 20℃; for 0.116667h;Green chemistry;	General procedure: A mixture of aldehyde (1 mmol), dimedone (1 mmol), ethyl acetoacetate (1 mmol) and ammonium acetate (1 mmol) was added to [2-MPyH]OTf catalyst (1 mol%) in water (2 mL), and the reaction mixture was stirred at room temperature for an appropriate time. Completion of the reactions was monitored by TLC (n-hexan/ethyl acetate 4:1). After completion of the reaction, the resulting solid crude product was filtered and then recrystallized from ethanol-water to obtain pure product. The formation of products was related by comparing the melting points, IR and NMR data with authentic samples and literature data.
96%	With [bis(N-phenyl-salicydenaminato)copper(II)]; ammonium acetate; In water; at 25℃; for 0.2h;Green chemistry;	General procedure: A mixture of dimedone (1.0 mmol), aldehyde (1.0mmol), ethyl acetoacetate (1.0 mmol), ammonium acetate(1.0 mmol) and Cu(II) Schiff-base complex as a catalyst (1mol%) in water (2 mL) was stirred at room temperature for an appropriate time. The progress of the reaction was monitored by TLC (n-hexan/ethyl acetate 5:1). After completion of the reaction, the resulting solid (crude product) was filtered and then recrystallized from ethanol-water to obtain pure product. The physical data (M.p, NMR,IR) of these known compounds were found to be identical with those reported in the literature.
96%	With ammonium acetate; In ethanol; at 20℃; for 0.116667h;	General procedure: A mixture of dimedone (1.0 mmol), aldehyde (1.0 mmol),ethyl acetoacetate (1.0 mmol), ammonium acetate (1.0 mmol)and nano SnO2 catalyst (1 mol%) in ethanol (2 ml) were stirredat room temperature for an appropriate time. The progress ofthe reaction was monitored by TLC (n-hexan/ethyl acetate 5:1).After completion of the reaction, the resulting solid (crude product) was filtered and then recrystallized from ethanol-water to obtain pure product. The physical data (mp, NMR, IR) of these known compounds were found to be identical withthose reported in the literature.

92%	With ammonium acetate; In neat (no solvent); at 70℃; for 0.25h;Ionic liquid; Green chemistry;	General procedure: A mixture of the aldehyde (1 mmol), dimedone or 1, 3-cyclohexanedione (1 mmol), ethyl acetoacetate (1 mmol), ammonium acetate (1 mmol), and DSIMHS (0.25 mmol) was heated in an oil bath (70 C) under stirring. The progress of the reaction was monitored by TLC (n-hexane/ethyl acetate, 8:2). After completion, the reaction mixture was washed with water, because DSIMHS is soluble in water, and the product was precipitated with high purity. Then the crude solid product was filtered off and recrystallized from ethanol.
87%	With ammonium acetate; In neat (no solvent); for 0.0666667h;Microwave irradiation;	General procedure: A mixture of aldehyde 1a-r (1 mmol), dimedone 2 (1 mmol), ammonium acetate 3(1.5 mmol), ethylacetoacetate 4 (1 mmol), and 23.4 mg of NiFe2O4 nanoparticles (10 mol%) were taken in a glass rod and irradiated in a microwave oven (500 W; when the reaction mixtures were placed under microwave irradiation, MW heating causes melting reactants that led to the partially liquefied reaction mixture and achieved fairly good mixing of the reactants with the catalyst). The progress of the reaction was checked by TLC (n-Hexane: EtOAc, 10:4). After completion, the resulting product was heated in ethanol. The catalyst was magnetically removed from the mixture and washed several times with ethanol for reuse. Then, the residue was poured into crushed ice and stirred for several minutes. The solid product was filtered and the pure product was obtained by recrystallization from hot ethanol-water.

Reference： [1]Journal of Molecular Liquids,2013,vol. 177,p. 44 - 48
[2]Combinatorial Chemistry and High Throughput Screening,2013,vol. 16,p. 782 - 787
[3]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 758 - 763
[4]Medicinal Chemistry Research,2014,vol. 23,p. 1031 - 1036
[5]Research on Chemical Intermediates,2016,vol. 42,p. 2047 - 2054
[6]Applied Organometallic Chemistry,2018,vol. 32
[7]Comptes Rendus Chimie,2011,vol. 14,p. 511 - 515
[8]Research on Chemical Intermediates,2016,vol. 42,p. 2487 - 2500
[9]RSC Advances,2016,vol. 6,p. 26026 - 26037
[10]Chirality,2012,vol. 24,p. 854 - 859

58
[ 126-81-8 ]
[ 122-03-2 ]
[ 135-19-3 ]
[ 1262726-63-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With rice husk; In neat (no solvent); at 90℃; for 0.833333h;Green chemistry;	General procedure: A mixture of 2-naphthol (1.0 mmol), aldehyde (1.0 mmol), 5,5-dimethyl-1,3-cyclohexadione (1.2 mmol) and RiH (0.5 g) was heated at 90 C. The reaction was monitored by TLC. After completion of the reaction, the mixture was diluted with acetone (10 mL) and filtered to separate the catalyst. The solvent was removed under reduced pressure. The crude product was purified by recrystalization in ethanol. The physical and spectral data of the known compounds were in agreement with those reported in literature [3,11,13].
90%	With 1,3-disulfonic acid imidazolium hydrogen sulfate; In neat (no solvent); at 55℃; for 0.583333h;Green chemistry;	General procedure: A mixture of beta-naphthol (1mmol), dimedone (1mmol), aldehyde (1mmol) and DSIMHS (0.25mmol) was stirred and heated in an oil-bath at 55C for an appropriate period of time. The reaction was monitored by TLC analyses. After the completion of the reaction, the reaction mixture was cooled to room temperature, 10mL of H2O was added, stirred for 5min and filtered to remove the catalyst. Then, 2mL of hot EtOH was added to the resulting solid product, stirred for 5min, and filtered. Finally, the solid residue was recrystallized from EtOH to give the pure product.
90%	With bis-2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepiniumethyl disulfate; In neat (no solvent); at 120℃; for 0.25h;Green chemistry;	General procedure: A mixture of cyclic 1,3-dicarbonyl (2 mmol), aldehydes (1 mmol), and [DBU]2[EDS] (40 mol%) was stirred at 120 C in oil bath for the time show in Table 2. Upon completion of the reaction as indicated by TLC (hexane:ethyl acetate, 8:2), hot EtOH (96%,1 ml) was added to the mixture which was stirred for 2 min. Then the reaction mixture was poured onto crushed ice and the precipitated solid was collected and recrystallized from ethanol (96%, 3 ml) to afford the pure 9-aryl-1,8-dioxo-octhydroxanthenes derivatives (2). Under the same conditions, this approach can be repeated for synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes, 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-1,6,10-ones, 14-aryl-14H-dibenzo[a,i]xanthenes-8,13-ones, 13-aryl-5H-dibenzo[b,i]xanthenes-5,7,12,14 (13H)-tetraones and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones.

89%	With 1H-imidazole; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry;	General procedure: To a mixture of beta-naphthol (1 mmol, 144.2 mg), aromatic aldehyde (1 mmol) and dimedone (1 mmol, 140.1 mg); imidazole (10 mol %, 6.8 mg) or isoquinoline (15 mol %, 19.4 mg) was added and heated in an oil bath at 80 C for the specific time indicated in Table 2. After completion of the reaction which was monitored by TLC, 5 mL of water was added to precipitate the product. The solid material was filtered, dried, and purified by recrystallization in ethanol.
88%	With phosphorus pentoxide; In neat (no solvent); at 120℃; for 0.416667h;Green chemistry;	General procedure: A mixture of 5,5-dimethyl-1,3-cyclohexanediones, substituted aromatic aldehyde, 2-naphthol and P2O5 as catalyst was stirred at 120 C in the oil bath. The reaction was monitored by TLC. The reaction was cooled to room temperature after completion of the reaction. The solid product was filtered, washed with hot water and finally recrystallized from ethanol. All the synthesized products were characterized by IR, NMR and mass spectroscopic data for their structure and their melting points were compared with authentic samples.
88%	With 4-[3-(4-sulfo-butyl)-imidazole-1-yl]-butane-1-sulfonate; 4-imidazol-1-yl-butane-1-sulfonate imidazolium; In neat (no solvent); at 50℃; for 0.5h;	General procedure: In a 25-mL round bottom flask, a mixture of aldehyde (1.0 mmol)and the desired substrates {dimedone (2.0 mmol) or 2-naphthol(2 mmol), or mixture of dimedone (1.0 mmol) and 2-naphthol(1.0mmol); according to Scheme 3} was heated and mixed in the presenceof ImBuSO3H (0.2 mL) at 50 C. The progress of the reaction was monitored by TLC. After completion of the reaction, the product was extractedwith EtOAc (3 × 5 mL), and the liquid salt (I + II) was recycled and was dried at 65 C under vacuum to remove moisture, and then was reused. The combined organic phases were concentrated under vacuum to afford the crude product. The highly pure product was obtained using silica gel column chromatography (n-hexane:ethyl acetate, 8:2) or recrystallization from hot ethanol. The isolated xanthenes were identified by comparison of their melting point, IR and NMR data with those reported in the literature.
80%	With N-sulfonic acid poly(4-vinylpyridinium) chloride; at 120 - 130℃; for 0.333333h;	General procedure: A mixture of beta-naphthol (0.144g, 1mmol), dimedone (1.2mmol), aldehyde (1mmol) and NSPVPC (20mg) was stirred in an oil-bath (120-130C). After completion of the reaction, as monitored with TLC, the reaction mixture was cooled, diluted with Et2O (5mL) and filtered to remove catalyst. The crude product was recrystallized from ethanol to afford the pure product. The spectral data of the selected compounds are as follow.

Reference： [1]Comptes Rendus Chimie,2013,vol. 16,p. 207 - 216
[2]Dyes and Pigments,2012,vol. 95,p. 789 - 794,6
[3]Chinese Chemical Letters,2014,vol. 25,p. 341 - 347
[4]Dyes and Pigments,2015,vol. 123,p. 222 - 234
[5]Research on Chemical Intermediates,2015,vol. 41,p. 4581 - 4586
[6]Asian Journal of Chemistry,2018,vol. 30,p. 804 - 806
[7]Journal of Molecular Liquids,2019,vol. 278,p. 19 - 32
[8]Research on Chemical Intermediates,2018,vol. 44,p. 4045 - 4062
[9]South African Journal of Chemistry,2014,vol. 67,p. 27 - 32
[10]Letters in Organic Chemistry,2012,vol. 9,p. 338 - 343
[11]Bulletin of the Chemical Society of Ethiopia,2011,vol. 25,p. 399 - 406
[12]Dyes and Pigments,2013,vol. 99,p. 250 - 255

59
[ 89-25-8 ]
[ 122-03-2 ]
[ 109-77-3 ]
[ 300731-67-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride; In ethanol; at 20℃; for 1h;	General procedure: Carbonyl compound (1.0 mmol), malononitrile (1.0 mmol) and aromatic aldehyde (1.0 mmol) were added in a 25.0 mL round-bottomed flask contained (SB-DBU)Cl (0.11 g, 5.0 mol%) and EtOH (5.0 mL). The resulting mixture was stirred at room temperature (method A) [in order of alkyl cyanoacetates, the reaction was carried out in EtOH/H2O (1:1) under reflux conditions (method B)]. After completion of the reaction, as monitored by TLC, ethanol (5 mL) was added to the reaction mixture and heated at 60 C for ?5 min to dissolve the product followed by centrifugation for 10 min to separate the (SB-DBU)Cl. The EtOH was evaporated under reduced pressure to give the crude product. The crude product was dissolved in warm EtOH or aqueous EtOH (6.0 mL) and was allowed to stand at room temperature for 3-5 h. The crystalline solids were collected, washed with ethanol and dried. The same procedure was applied for the preparation of spiro-pyran derivatives and complex compounds; however, in the case of the preparation of complex compounds, 2.0 mmol of carbonyl compound, 2.0 mmol of alkylmalonate and 1.0 mmol of dialdehyde were used. The recovered (SB-DBU)Cl was reused for another time without loss of its activity. 3.14 ;6-Amino-4-(4-isopropylphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (6x) ;M.p. = 156-180 C. 1H NMR (DMSO-d6, 500 MHz): delta 1.19 (d, J = 8.3 Hz, 6H), 1.79 (s, 3H), 2.86 (m, 1H), 4.63 (s, 1H), 7.16-7.71 (m, 11H).13C NMR (DMSO-d6, 125 MHz): delta 13.3, 32.8, 59.4, 99.5, 120.6, 120.8, 125.8, 126.3, 127.1, 127.5, 130.2, 138.2, 144.3, 146.2, 149.6, 160.0. Anal. Calcd. for C23H22N4O: C, 74.57; H, 5.99; N, 15.12. Found: C, 74.73; H, 5.63; N, 15.19.
92%		General procedure: To a mixture of 6 mL water and ethanol (1:2) in a round bottom flask, 1.25 mmol (0.082 g) malononitrile and 1 mmol aryl aldehyde were added. Then 0.01 mmol (0.018 g) SSC was added to this mixture. After stirring the reaction mixture for 2 h at 80 C, 0.88 mmol (0.153 g) 3-methyl-1-phenyl-2-pyrazolin-5-one was added to the reaction mixture. Reaction progress was controlled by TLC. After 20-40 min the reaction was completed. Then, the reaction mixture for the separation of catalyst was filtrated and the catalyst was washed with ethanol, dried at 120 for 2 h and was reused in another reaction. The filtrate was poured on a few small pieces of ice in a small beaker to appear as pure crystal products. Then crystalline product was filtrated, collected and characterized by FT-IR, 1H NMR, 13C NMR, elemental analyses (C, H, N) and via comparison of their melting points with the reported ones for known compounds.
92%	With tungstate sulfuric acid; In ethanol; at 70 - 80℃; for 0.583333h;Green chemistry;	General procedure: A mixture of 3-methyl-1-phenyl-2-pyrazolin-5-one (1 mmol), aromatic aldehyde (1 mmol), malononitrile (1 mmol), and TSA (10 mol%) in ethanol (10 mL) was refluxed for an appropriate period of time. After the completion of the reaction (monitored by TLC analysis), the catalyst was separated by filtration. The solvent was removed under vacuum and the products 7 were purified by recrystallization from EtOH/H2O.

92%	With silica sodium carbonate; In ethanol; water; at 80℃; for 0.583333h;	General procedure: To a mixture of 6mL water and ethanol (1:2) in a round bottom flask, 1.25 mmol (0.082 g) malononitrile and 1 mmol aryl aldehyde were added. Then 0.01 mmol (0.018 g) SSC was added to this mixture. After stirring the reaction mixture for 2 h at 80C, 0.88 mmol (0.153g) 3-methyl-1-phenyl-2-pyrazolin-5-one was added to the reaction mixture. Reaction progress was controlled by TLC. After 20-40 min the reaction was completed. Then, the reaction mixture for the separation of catalyst was filtrated and the catalyst was washed with ethanol, dried at 120C for 2h and was reused in another reaction. The filtrate was poured on a few small pieces of ice in a small beaker to appear as pure crystal products. Then crystalline product was filtrated, collected and characterized by FT-IR, 1H NMR, 13C NMR, elemental analyses (C, H, N) and via comparison of their melting points with the reported ones for known compounds.
85%	With sodium bromide; In ethanol; at 25℃; for 0.333333h;Electrolysis; Green chemistry;	General procedure: A mixture of aryl aldehyde (2 mmol), malononitrile (3 mmol), 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (2 mmol), and NaBr (0.05 g, 0.5 mmol) in EtOH (20 mL) was electrolyzed in an undivided cell equipped with a magnetic stirrer, a graphite anode, and an iron cathode at 25 C under a constant current density of 10 mA/cm2 [electrodes square 5 cm2] until the catalytic quantity of 0.62 F/mol of electricity was passed. After the electrolysis was finished, the precipitated products were separated by filtration which was then twice rinsed with an ice-cold ethanol/water solution (9:1, 5 mL), and dried under reduced pressure.

Reference： [1]Applied Catalysis A: General,2011,vol. 402,p. 11 - 22
[2]Green Chemistry,2012,vol. 14,p. 1696 - 1704
[3]Journal of Molecular Catalysis A: Chemical,2013,vol. 372,p. 137 - 150
[4]Catalysis Communications,2014,vol. 54,p. 124 - 130
[5]Chinese Chemical Letters,2014,vol. 25,p. 1580 - 1582
[6]Catalysis Communications,2014,vol. 54,p. 124 - 130
[7]Chinese Chemical Letters,2015,vol. 26,p. 973 - 976

60
[ 122-03-2 ]
[ 13816-33-6 ]
[ 3717-17-7 ]

Yield	Reaction Conditions	Operation in experiment
10%; 84%	With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In dichloromethane; for 24h;Reflux;	4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10% SE-30 on Chromosorb, 10' × 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97%).
80%; 12%	With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In N,N-dimethyl-formamide; for 24h;Reflux;	4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10% SE-30 on Chromosorb, 10' × 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97%).

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3421 - 3424
[2]Tetrahedron Letters,2012,vol. 53,p. 3421 - 3424

61
[ 21047-57-4 ]
[ 122-03-2 ]
[ 23152-99-0 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4070 - 4073

62
[ 317595-54-3 ]
[ 122-03-2 ]
[ 1416225-79-0 ]

Reference： [1]Archiv der Pharmazie,2012,vol. 345,p. 896 - 901

63
[ 64-18-6 ]
[ 122-03-2 ]
[ 4395-92-0 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 6277 - 6282
Angew. Chem.,2013,vol. 125,p. 6397 - 6402,6

64
[ 57497-39-9 ]
[ 122-03-2 ]
4-isopropylbenzylidene t-butylamine N-oxide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6531 - 6535

65
[ 122-03-2 ]
[ 2476-29-1 ]
[ 1448349-06-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 6033 - 6053

66
[ 96145-98-1 ]
[ 122-03-2 ]
[ 1439908-50-5 ]

Reference： [1]Medicinal Chemistry Research,2014,vol. 23,p. 158 - 167

67
[ 60-35-5 ]
[ 575-03-1 ]
[ 122-03-2 ]
N-((7-hydroxy-2-oxo-4-(trifluoromethyl)-2H-chromen-8-yl)(4-isopropylphenyl)methyl)acetamide [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 14501 - 14506

68
[ 88-96-0 ]
[ 126-81-8 ]
[ 122-03-2 ]
[ 1245471-24-2 ]

Reference： [1]Dalton Transactions,2015,vol. 44,p. 5888 - 5897

69
[ 19947-39-8 ]
[ 122-03-2 ]
4-(isocyanomethyl)benzonitrile [ No CAS ]
2-(2-(4-chlorophenyl)-4-oxoazetidin-1-yl)-N-(4-cyanobenzyl)-2-(4-isopropylphenyl)acetamide [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2002 - 2005

70
[ 1003-04-9 ]
[ 122-03-2 ]
(2Z,4Z)-2,4-bis(4-isopropylbenzylidene)dihydrothiophen-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide; In ethanol; water; at 20℃; for 2h;	General procedure: A solution of NaOH (1 mmol) in 1 mL of water was added to a mixture of dihydrothiophen-3(2H)-one (1, 1 mmol) and the appropriate aldehydes (2 mmol) in 10 ml of ethanol. The mixture was stirred at room temperature for 2 h and the reaction progress was monitored by TLC analysis. After completion of the reaction, the precipitate obtained was filtered and washed with cold ethanol to afford 2 as yellow solid.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 5805 - 5807

71
[ 122-03-2 ]
[ 5202-85-7 ]
6-chloro-2-(4-isopropylphenyl)-2,3-dihydroquinazolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With indium(III) bromide In acetonitrile at 20℃; for 0.666667h;	1.2 General Procedure for Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones (3a-3aa) General procedure: Indiumtribromide (0.5 mol %) was added to a solution of 2-amino benzanilide or 2-amino-5-chloro benzamide (1 mmol) and desired aldehydes (1 mmol) in acetonitrile (3mL). The mixture was stirred at room temperature for the specified period of time. The progress of the reaction was monitored by TLC. After completion of reaction, solvent was evaporated at reduced pressure, and solid was partitioned between ethyl acetate (15.0 mL) and water (15.0mL), and transferred to a separatory funnel. The organic layer was washed with water, and brine, dried over anhydrous Na2SO4 (s) and concentrated in vacuo. The residue was purified by recrystallization from CH2Cl2/Hexane to afford the corresponding pure 2,3-dihydroquinazolin-4(1H)-ones (3a-3aa) as solids with excellent yields.

Reference： [1]Rajaka, Lingayya; Penumati, Nageshwar Rao; Nagaiah; Poornachandra; Kumar, C. Ganesh [Synthetic Communications, 2015, vol. 45, # 16, p. 1893 - 1901]

72
[ 33228-44-3 ]
[ 122-03-2 ]
[ 109-77-3 ]
[ 623-47-2 ]
C₂₉H₃₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 4-pentylaniline; propynoic acid ethyl ester In ethanol at 20℃; for 10h; Stage #2: (4-isopropylbenzaldehyde); malononitrile With triethylamine In ethanol at 20℃; for 2h;	Typical experimental procedure for the synthesis of N-Substituted 1,4- dihydropyridines 5h General procedure: In a round-bottom flask, a mixture of aniline (1 equivalent, 0.2 g) and ethyl propiolate (1 equivalent, 0.208 g)in 5.0 mL of ethanol was stirred at room temperature for 10 h. Then, aromatic aldehyde (1 equivalent, 0.292 g), malononitrile (1 equivalent, 0.217 g) and triethylamine (1 equivalent, 0.141 g) in 5.0mL of ethanol were added. The solution was stirred at a room temperature for additional two hours. After completion of the reaction, the solvent was removed under reduced pressure. The solid product was collected by filtration and washed with cold ethanol to give the pure product 5h without further purification or recrystallization.

Reference： [1]Dhinakaran, Isaivani; Padmini, Vediappen; Bhuvanesh, Nattamai [Journal of Chemical Sciences, 2015, vol. 127, # 12, p. 2201 - 2209]

73
[ 29096-60-4 ]
[ 122-03-2 ]
C₂₀H₂₀N₂O [ No CAS ]

Reference： [1]Comptes Rendus Chimie,2016,vol. 19,p. 850 - 856

74
[ 874-05-5 ]
[ 126-81-8 ]
[ 122-03-2 ]
7-(4-isopropylphenyl)-10,10-dimethyl-7,9,10,11-tetrahydroindazolo[3,2-b]quinazolin-8(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron(III) trifluoride; In neat (no solvent); at 80℃; for 0.05h;Sonication; Green chemistry;	General procedure: To a 10 mL vessel was added <strong>[874-05-5]1H-indazol-3-amine</strong>s (1, 1 mmol), aldehydes (2, 1 mmol), and 1,3-dicarbonyl compounds (3, 1 mmol), and FeF3 (10 mol %) the reaction was carried out under ultrasound (20 KHz, 80 C). The resulting solution was sonicated with a US probe for the time indicated in Table 2. After completion of the reaction, as indicated by TLC, reaction diluted with water precipitate product separated out by simple filtration washed with water and dried to afford the pure products 4. The FeF3 catalyst was dissolved in water and also recovered by evaporating the aqueous layer under reduced pressure.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3795 - 3799

75
[ 582-24-1 ]
[ 122-03-2 ]
[ 92831-11-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1-butyl-3-methylimidazolium chromate; oxygen In butan-1-ol at 60℃; for 3h;	10 Example 10: synthesis of 4'-isopropylflavone In 10 ml in the reaction kettle, successively added 0.2964g (2mmol) 4-isopropyl-benzaldehyde, 0.2723g (2mmol) 2-hydroxy acetophenone and 0.1578g (0.4mmol) of the ionic liquid catalyst [Bmim]2[CrO4] (refer to the embodiment of the structural formula 5), and 0.4447g (6mmol) butanol solvent, stirring after mixing, heating to reaction temperature 60 °C, in 0.1 MPa stir to react under oxygen atmosphere 3h, after the reaction cooled to room temperature, water extraction, static split-phase, through the corresponding solvent is removed by reduced pressure distillation after the n-butyl alcohol, and recrystallization to column chromatography separation to obtain the target product 4'-isopropyl flavone, the yield is 95%, the nuclear magnetic resonance hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry to determine its structural formula is:

Reference： [1]Current Patent Assignee: JIANGXI NORMAL UNIVERSITY - CN105294627, 2016, A Location in patent: Paragraph 0065; 0066; 0067

76
[ 122-03-2 ]
[ 10528-64-0 ]

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 1678 - 1685

77
[ 2221-00-3 ]
[ 134-81-6 ]
[ 122-03-2 ]
4,5-diphenyl-1-[4-(1H-imidazol-1-yl)phenyl]-2-(4-isopropylphenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With bismuth (III) nitrate pentahydrate; ammonium acetate; silica gel; In neat (no solvent); at 110℃; for 24h;	General procedure: A mixture of N-(4-aminophenyl) azoles 2a-d (1 mmol), benzil (1 mmol, 0.21 g), aromatic aldehyde (1 mmol), and ammonium acetate (1 mmol, 0.077 g) was stirred vigorously. Bi(NO3)3*5H2O (0.15 mmol, 0.073 g, 15 mol%) and SiO2 (0.5 g) were mixed effectively and added to the mixed reactants. The resulting mixture was heated at 110 C for 24 h. Acetone (50 mL) was then added and the mixture was stirred at 50 C for 10 min. Filtering the hot mixture and then concentration of the filtrate produced the crude product. Recrystallization of the crude products in 96% EtOH gave the desired product 3-5.

Reference： [1]Turkish Journal of Chemistry,2016,vol. 40,p. 729 - 741

78
[ 17635-45-9 ]
[ 134-81-6 ]
[ 122-03-2 ]
4,5-diphenyl-2-(4-isopropylphenyl)-1-[4-(1H-pyrazol-1-yl)phenyl]-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With bismuth (III) nitrate pentahydrate; ammonium acetate; silica gel; In neat (no solvent); at 110℃; for 24h;	General procedure: A mixture of N-(4-aminophenyl) azoles 2a-d (1 mmol), benzil (1 mmol, 0.21 g), aromatic aldehyde (1 mmol), and ammonium acetate (1 mmol, 0.077 g) was stirred vigorously. Bi(NO3)3*5H2O (0.15 mmol, 0.073 g, 15 molpercent) and SiO2 (0.5 g) were mixed effectively and added to the mixed reactants. The resulting mixture was heated at 110 °C for 24 h. Acetone (50 mL) was then added and the mixture was stirred at 50 °C for 10 min. Filtering the hot mixture and then concentration of the filtrate produced the crude product. Recrystallization of the crude products in 96percent EtOH gave the desired product 3-5.

Reference： [1]Turkish Journal of Chemistry,2016,vol. 40,p. 729 - 741

79
[ 874-05-5 ]
[ 98-86-2 ]
[ 122-03-2 ]
4-(4-isopropylphenyl)-2-phenylpyrimido[1,2-b]indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydroxide; In N,N-dimethyl-formamide; at 125℃; for 9h;	To a mixture of <strong>[874-05-5]1H-indazol-3-amine</strong> (1 mmol), aldehyde (1 mmol) and acetophenone (1 mmol)in 5 mL of dimethylformamide potassium hydroxide (2.2 mmol) was added at room temperature.The reaction mixture was heated to 125 C for 9 h. The progress of the reaction was monitored byTLC. After the completion of the reaction, the mixture was poured into crushed ice. The mixture wasextracted by ethyl acetate and water. The organic layer was separated and dried over sodium sulphateand the solvent evaporated. The crude product was purified by column chromatography to afford the product as a solid. 4-(4-Isopropylphenyl)-2-phenylpyrimido[1,2-b]indazole (4b); Brown solid; Isolated yield 86%; m.p.:170-172 C; 1H-NMR (CDCl3) delta 8.42 (d, J = 8.0 Hz, 1H), 8.28-8.26 (m, 2H), 8.18-8.16 (m, 2H),7.96-7.85 (m, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.74 (s, 1H), 7.63-7.549 (m, 7H), 7.32-7.28 (m, 1H),3.08-3.01 (m, 1H), 1.35 (d, J = 6.8 Hz, 6H); 13C-NMR (CDCl3) delta 23.8, 34.3, 108.4, 113.9, 116.5, 120.6, 121.2, 126.5, 127.0, 127.2, 128.0, 128.3, 128.5, 129.0, 129.2, 129.5, 130.0, 133.0, 137.4, 145.0, 145.4, 151.6,152.2, 152.6; HRMS (EI): m/z calcd. for C25H21N4 363.1735 found 363.1735.

Reference： [1]Molecules,2016,vol. 21

80
[ 68176-57-8 ]
[ 122-03-2 ]
5-(tert-butyl)-2-(4-isopropylphenyl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In ethanol; at 80℃; for 2h;	General procedure: ZrO2-Al2O3 solid acid catalytic material was added to the stirred solution of O-phenylenediamines and different substituted aromatic aldehydes in a suitable solvent, and the resulting mixture was heated at a particular temperature and monitored by TLC. After the completion of the reaction, the reaction mixture was cooled and filtered and the residue was washed with ethanol to recover the solid acid catalyst. Filtrate was evaporated in vacuum to get the crude reaction product, which was then purified by silica-gel column chromatography using a suitable mobile phase to separate the desired product. The reaction products were characterized by melting point, 1H NMR and 13C NMR spectroscopy (Bruker, 400 MHz), LC-MS (Varian), and HPLC (Waters) techniques

Reference： [1]Synthetic Communications,2016,vol. 46,p. 1537 - 1559

81
[ 16182-15-3 ]
[ 122-03-2 ]
C₁₉H₂₄N₂O₂S [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 837 - 841
Angew. Chem.,2017,vol. 129,p. 855 - 859,5

82
[ 4569-77-1 ]
[ 122-03-2 ]
[ 109-77-3 ]
3,5-diamino-1-(4-isopropylphenyl)-1H-pyrano[3,2-a]phenazine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol;Reflux;	General procedure: Compounds 12 (1 mmol), 13 (1 mmol), 14 (1 mmol) were addedto a 25-mL round-bottomed flask containing DABCO (0.3 mmol) inethanol (10 mL). The flask was fitted with a condenser, and theresulting mixture was heated to reflux under stirring. Aftercompletion of the reaction (0.5-2.5 h), as monitored by TLC, thereaction mixture was allowed to cool to room temperature andthen washed with saturated sodium carbonate solution for threetimes. The solid product was filtered off, washed with deionizedwater for three times, dried in vacuo, and subsequently recrystallizedfrom hot ethanol to give the final products.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 928 - 943

83
[ 94-45-1 ]
[ 122-03-2 ]
[ 121-45-9 ]
dimethyl (((6-ethoxybenzo[d]thiazol-2-yl)amino)(4-isopropylphenyl)methyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With nitrogen-sulfur-doped carbon spheres; In neat (no solvent); at 50℃; for 0.533333h;	General procedure: (CN-CSs) (3 mg) was added to a mixture of aldehydes (1 mmol), 2-aminobenzothiazoles (1 mmol) and trimethylphosphite (1 mmol, 0.12 gr), and the mixture was stirredat 50 C. After completion of the reaction as monitored byTLC, the mixture was washed with CH2Cl2(3 × 3 mL). The combined extracts were filtered, and the solvent was removed under reduced pressure. The product was purifiedby column chromatography by using hexane-ethyl acetateas solvent system in different concentration to obtain the pure compound.

Reference： [1]Journal of the Iranian Chemical Society,2017,vol. 14,p. 1971 - 1982

84
[ 4395-73-7 ]
[ 122-03-2 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 3843 - 3848

85
[ 80041-89-0 ]
[ 17763-69-8 ]
[ 122-03-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909

86
[ 7025-19-6 ]
[ 122-03-2 ]
(Z)-3-(5-(4-isopropylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium acetate; acetic acid; at 105℃;Inert atmosphere;	General procedure: To a mixture of aldehyde (1.0 mmol), <strong>[7025-19-6]3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid</strong> (205 mg,1.0 mmol) or 3-(2-(1H-tetrazol-5-yl)ethyl)-2-thioxothiazolidin-4-one (229 mg, 1.0 mmol) and NaOAc (820 mg, 10.0 mmol) was added acetic acid (5.0 mL). The reaction was allowed to stir at 105 C for 0.5h - 12h, then cooled to room temperature. To the reaction was added water (15mL). The resulting mixture was sonicated to give yellow-orange slurry. After filtration, the solid was washed with water (75 mL) and dried under high vacuum to yield the corresponding product as a red fine powder.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1024 - 1029

87
[ 98-18-0 ]
[ 122-03-2 ]
3-((4-isopropylbenzyl)amino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: To a solution of 3-aminobenzenesulfonamide (1.0 equiv) and acetic acid (1.2 equiv) stirred in anhydrous dichloromethane (0.1M) with 4 molecular sieves was added aldehyde (1.2 equiv). The solution was then stirred for 30min. Next, Na(OAc)3BH3 (2.0 equiv) was added in portions and then reaction allowed to stir at room temperature overnight. When TLC indicated the reaction was complete, the reaction was filtered and the solution was concentrated, loaded on silica gel, and purified by flash column chromatography with petroleum/ethyl acetate as eluent to give 1 and 17. 4.1.1.1 56 3-((4-isopropylbenzyl)amino)benzenesulfonamide (1) Yield 96percent, white solid, 1H NMR (500MHz, DMSO-d6) delta 7.27 (d, J=7.9Hz, 2H), 7.24?7.15 (m, 5H), 7.08 (t, J=2.1Hz, 1H), 6.96 (dt, J=7.9, 1.0Hz, 1H), 6.74?6.70 (m, 1H), 6.68 (t, J=6.0Hz, 1H), 4.25 (d, J=5.9Hz, 2H), 2.86 (hept, J=6.9Hz, 1H), 1.18 (d, J=6.8Hz, 6H).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 151,p. 752 - 764

88
[ 617-89-0 ]
[ 20577-61-1 ]
[ 122-03-2 ]
4-acetyl-3-hydroxy-5-(4-isopropylphenyl)-1-(2-furylmethyl)-3-pyrrolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With acetic acid; In ethanol; at 20℃; for 24h;Heating;	General procedure: Acetic acid (1.04 mL) was added to a mixture of acetylpyruvic acid methyl ester (1.44 g, 0.01 mol), bezaldehyde (1.06 g, 0.01 mol), and furfurylamine (0.97 g, 0.01 mol) in 10 mL of ethanol. The reaction mixture was heated for 15 min and kept at room temperature for 1 day. The precipitate was filtered off and recrystallized from acetonitrile.

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 598 - 601
Zh. Obshch. Khim.,2018,vol. 88,p. 508 - 511,4

89
[ 5153-67-3 ]
[ 100643-27-4 ]
[ 122-03-2 ]
2-amino-7-(4-isopropylphenyl)-6-nitro-5-phenyl-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4(3H)-one [ No CAS ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 2057 - 2063

90
[ 100643-27-4 ]
[ 101671-00-5 ]
[ 122-03-2 ]
2-amino-7-(4-isopropylphenyl)-6-nitro-5-(p-tolyl)-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-4(3H)-one [ No CAS ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 2057 - 2063

91
[ 30568-44-6 ]
[ 122-03-2 ]
(E)-1-(4-isopropylphenyl)-N-(2-(4-methoxyphenyl)propan-2-yl)methanimine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 12h; Molecular sieve;

Reference： [1]Yamashita, Yasuhiro; Suzuki, Hirotsugu; Sato, Io; Hirata, Tsubasa; Kobayashi, Shū [Angewandte Chemie - International Edition, 2018, vol. 57, # 23, p. 6896 - 6900][Angew. Chem., 2018, vol. 130, # 23, p. 7012 - 7016,5]

92
[ 6090-09-1 ]
[ 122-03-2 ]
(E)-3-(4-isopropylphenyl)-1-(4-methylcyclohex-3-en-1-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydroxide; In ethanol; water; at 20℃; for 2h;	General procedure: In a round-bottomed flask, a mixture of limona ketone(3.6 mmol, 0.5 g), an aromatic aldehyde (3.6 mmol) in ethanol(5 mL) and NaOH (3.6 mmol) in water (5 mL) was added. The mixture was stirred at room temperature for the indicated time. At the end of the reaction, which was monitored by thin-layer and gas chromatography, the mixture was diluted with 30 mL of water and extracted 3 times with 20mL of EtOAc. The organic layer was concentrated and the residue was purified by using silica gel column chromatography with Hexane-EtOAc as eluent. The obtained pure monoaryledine was characterized by spectroscopic analysis

Reference： [1]Letters in Organic Chemistry,2018,vol. 15,p. 698 - 704

93
[ 31301-51-6 ]
[ 122-03-2 ]
(6-chloro-3-fluoropyridin-2-yl)(4-isopropylphenyl)methanol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 10748 - 10751
Angew. Chem.,2018,vol. 130,p. 10908 - 10911,4

94
[ 423165-07-5 ]
[ 4426-72-6 ]
[ 122-03-2 ]
N'-{(4-propane-2-ylphenyl)-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]methyl}-hydrazine carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.82%	With ammonium hydroxide; In methanol; water; for 2h;Cooling with ice;	General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

Reference： [1]Asian Journal of Chemistry,2018,vol. 30,p. 2029 - 2034

95
[ 423165-07-5 ]
[ 79-19-6 ]
[ 122-03-2 ]
N'-{(4-propane-2-ylphenyl)-[3-(3-isopropyl-5-methyl-[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]methyl}-hydrazine carbothiamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.27%	With ammonium hydroxide; In methanol; water; for 2h;Cooling with ice;	General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

Reference： [1]Asian Journal of Chemistry,2018,vol. 30,p. 2029 - 2034

96
[ 423165-07-5 ]
[ 1443256-99-2 ]
[ 122-03-2 ]
4,4-difluorocyclohexanecarboxylic acid N'-[[(3-(3-isopropyl-5-methyl)[1,2,4]triazol-4-yl)-8-azabicyclo[3.2.1]-oct-8-yl]-(4-isopropylphenyl)methyl]hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With ammonium hydroxide; In methanol; water; for 2h;Cooling with ice;	General procedure: To an aqueous solution of active hydrogen containing amide, few drops of aqueous ammonia solution (1 eq.) and secondary amine (1 eq.) were added in drops in an ice-cold solution under constant stirring for dissolution. Aromatic aldehydes dissolved in methanol, added dropwise to the above mixture and stirring was continued for 2 h. The formation of compounds were observed within 30 min. Reaction was monitored by TLC, after completion of reaction, the product was filtered and washed with distilled water and dried at 45-50 C.

Reference： [1]Asian Journal of Chemistry,2018,vol. 30,p. 2029 - 2034

97
[ 61-54-1 ]
[ 20577-61-1 ]
[ 122-03-2 ]
[ 697238-36-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	In 1,4-dioxane; at 20℃; for 24h;Heating;	General procedure: To a mixture of 0.01 mol of aromatic aldehyde and 0.01 mol of tryptamine in 50 mL of dioxane was added 0.01 mol of methyl acetylpyruvate. The mixture was heated till the reagents dissolution and then stirred at room temperature for 1 day. The formed precipitate was filtered off and recrystallized from ethanol.

Reference： [1]Russian Journal of General Chemistry,2018,vol. 88,p. 1270 - 1272
Zh. Obshch. Khim.,2018,vol. 88,p. 1048 - 1050,3

98
[ 100643-27-4 ]
[ 122-03-2 ]
2,8-diamino-5-(4-isopropylphenyl)-5,10-dihydropyrido[2,3-d:6,5-d']dipyrimidine-4,6(3H,7H)-dione [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2270 - 2276

99
[ 122-03-2 ]
[ 135-19-3 ]
[ 2274-42-2 ]
2-amino-3-methylsulfonyl-4-(4-isopropylphenyl)-4H-benzochromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With (2-hydroxy-ethyl)ammonium acetate; In water; under 760.051 Torr; for 5h;	In a three-necked flask p-isopropylbenzaldehyde (148.1 mg, 1 mmol), beta-naphthol (144.1 mg, 1 mmol), methylsulfonyl acetonitrile (119.1 mg, 1 mmol), HEAA (24.2 mg, 0.2 mmol) and H2O (5 mL) were added and stirred at normal temperature and pressure for 5 h. After the reaction was completed, the resulting mixture was filtered at atmospheric pressure, the filter cake was collected, washed with ethanol three times, and dried to obtain pale yellow target product of 2-amino-3-methylsulfonyl-4-(4-isopropylphenyl)-4H-benzochromene in a yield of 79%.

Reference： [1]Patent: CN108586419,2018,A .Location in patent: Paragraph 0032

100
[ 122-03-2 ]
[ 100987-89-1 ]

Reference： [1]Catalysis Letters,2018,vol. 148,p. 3486 - 3491

101
[ 20356-45-0 ]
[ 6752-16-5 ]
[ 122-03-2 ]
4-(4-isopropylphenyl)-2-(1H-indol-3-yl)pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With N,N,N',N'-tetramethylguanidine; In neat (no solvent); at 120℃;Green chemistry;	General procedure: The TMG (2.5 mmol) was added to a mixture of <strong>[6752-16-5]1H-pyrazolo[3,4-b]pyridin-3-amine</strong> (1, 1.0 mmol), aromatic aldehyde (2, 1.0 mmol) and 3-(1H-indol-3-yl)-3-oxopropanenitrile (3, 1.0 mmol) reaction flask equipped with a magnetic stirrer. The resulting mixture was stirred for the appropriate time at 120 C. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. Then added water for removal of TMG from the reaction mixture, it was miscible in water and stirring continued till a free-flowing solid was obtained. The resulting solid product was filtered and washed with water. The obtained crude product was recrystallized from ethanol to yield the pure products 4.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 2663 - 2674

102
[ 122-03-2 ]
[ 7605-28-9 ]
[ 135-19-3 ]
2-amino-3-phenylsulfonyl-4-(4-isopropylphenyl)-4H-naphthopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1-butyl-3-methylimidazolium hydroxide; In water; at 25℃; under 760.051 Torr; for 8h;Green chemistry;	In a three-necked flask, 4-isopropylbenzaldehyde (148.1 mg, 1 mmol), beta-naphthol (144.1 mg, 1 mmol), Benzene sulfonyl acetonitrile (199.3 mg, 1.1 mmol), [bmim]OH (31.2 mg, 0.2 mmol) And H2O (5mL), stirring at 25 C under normal pressure for 8 h, After the reaction is completed, Filter and collect the filter cake at atmospheric pressure. Washed with ethanol three times, After drying, the title compound was obtained as white product: 2-amino-3-phenylsulfonyl-4-(4-isopropyl-phenyl)-4H-naphthopyran, yield 84%.

Reference： [1]Patent: CN108623553,2018,A .Location in patent: Paragraph 0067-0069

103
[ 100643-27-4 ]
[ 126-81-8 ]
[ 122-03-2 ]
2-amino-5-(4-isopropylphenyl)-8,8-dimethyl-5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-4,6(3H,7H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With MIL-100(Cr)/NHEtN(CH2PO3H2)2; In N,N-dimethyl-formamide; at 100℃; for 0.333333h;	General procedure: In a 10 mL round-bottomed flask, a mixture of aldehyde (1 mmol),uracil derivatives (1 mmol), dimedone (1 mmol, 0.14 g) and MIL-100(Cr)/NHEtN(CH2PO3H2)2 (0.01 g) were stirred at 100 C in DMF(5 ml) as solvent. After completion of the reaction as monitored by TLC,the reaction mixture was cooled to room temperature. Then, the catalystwas separated from the solution of reaction mixture by centrifugation(1000 rpm). Then, H2O (5 ml) was added to reaction mixtureto give the solid sediment. The prepared solid was collected by simplefiltration. The crude product was purified by recrystallization fromEtOAc (Scheme 3). The pure products were identified by FT-IR, 1H, 13CNMR and mass spectra.

Reference： [1]Molecular catalysis,2020,vol. 481

104
[ 558-13-4 ]
[ 122-03-2 ]
[ 23152-99-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 611 - 616

105
[ 122-03-2 ]
[ 196597-78-1 ]
(E)-7-(4-isopropylbenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2019

106
[ 1620805-30-2 ]
[ 122-03-2 ]
[ 2274-42-2 ]
(E)-4-(4-isopropylphenyl)-6-methyl-3-(methylsulfonyl)-8-(4-[trifluoromethyl]benzylidene)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridin-2-amine [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2020,vol. 67,p. 821 - 828

107
[ 7142-09-8 ]
[ 122-03-2 ]
6-chloro-2-{(E)-2-[4-(propan-2-yl)phenyl]ethenyl}quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sulfuric acid; at 190℃; under 750.075 - 5250.53 Torr; for 1.5h;Microwave irradiation;	General procedure: The 2-methylquinazolin-4(3H)-ones (1 mmol) were mixed with benzaldehydes (1.5 mmol) and 1 drop concentrated sulphuric acid was added to the mixtures. The reaction was carried out in microwave set (Personal Chemistry, Emrys Creator, heating power: 150 W, measured pressure 1-7 bar, reaction time: 1.5 hours) at 190 C. The crude product was washed with 5% sodium hydrogen carbonate and filtered out. The products were crystallized from dimethyl formamide and dried under vacuum.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 184

108
[ 719-98-2 ]
[ 122-03-2 ]
S-(trifluoromethyl)-4-isopropylbenzothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With disodium hydrogenphosphate; tetrakis(tetrabutylammonium)decatungstate(VI); In acetonitrile; at 20.0℃; for 96.0h;Inert atmosphere; Sealed tube; Irradiation;	General procedure: To a 8 mL glass vial was added TBADT (54.4 mg, 0.016 mmol, 8 mol %), aldehydes (0.2 mmol, 1.0 equiv), 6a (148.3 mg, 0.6 mmol, 3.0 equiv), Na2HPO4 (42.6 mg, 0.3 mmol, 1.5 equiv) and 0.5mL of CH3CN. The reaction mixture was degassed by bubbling with Ar for 15 s with an outlet needle and the vial was sealed with PTFE cap. The mixture was then stirred rapidly and irradiated with a 390 nm Blue LED (approximately 2 cm away from the light source) at room temperature for 96 h. Purification of the crude product by flash chromatography on silica gelusing the indicated solvent system afforded the desired product.

Reference： [1]Chinese Chemical Letters,2021,vol. 32,p. 3027 - 3030

109
[ 137-07-5 ]
[ 122-03-2 ]
[ 16112-21-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica supported phosphomolybdic acid; air; In dichloromethane; at 20℃;	General procedure: To a mixture of 2-aminophenol (or 2-aminothiophenol)(1mmol) and aryl aldehyde (1 mmol) in CH2Cl2 (5mL)PMA.SiO2 (113 mg) was added. The mixture was stirred atroom temperature and the reaction was monitored by TLC.After completion, the mixture was filtered and the catalystwas recovered after washing the residue with EtOAc (3×5mL). The filtrate was concentrated to afford a gummy mass. On the other hand, to obtain a pure benzothiazole, theresidue was dissolved in EtOH (10 mL) and the solution waspoured onto ice-cold water (20 mL) to furnish solid productwhich was filtered, washed with ice-cold water and subsequentlydried. The recovered catalyst was recycled threetimes without affecting the yield of the product.

Reference： [1]Letters in Organic Chemistry,2021,vol. 18,p. 583 - 587

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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkylation of Aldehydes or Ketones • Amides Can Be Converted into Aldehydes • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Conversion of Amino with Nitro • Convert Aldonic Acid into the Lower Aldose by Oxidative Decarboxylation • Convert Esters into Aldehydes Using a Milder Reducing Agent • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Deprotonation of Methylbenzene • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Dithioacetal Formation • Electrophilic Chloromethylation of Polystyrene • Enamine Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Dihydropyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration of a Terminal Alkyne • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nitration of Benzene • Nozaki-Hiyama-Kishi Reaction • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Periodic Acid Degradation of Sugars • Petasis Reaction • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reduction of an Ester to an Aldehyde • Reductive Amination • Reductive Removal of a Diazonium Group • Reformatsky Reaction • Reverse Sulfonation——Hydrolysis • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Selective Eduction of Acyl Chlorides to Produce Aldehydes • Stetter Reaction • Stobbe Condensation • Strecker Synthesis • Sulfonation of Benzene • Synthesis of 2-Amino Nitriles • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 122-03-2 ] {[proInfo.proName]}

Quality Control of [ 122-03-2 ]

Related Doc. of [ 122-03-2 ]

Product Details of [ 122-03-2 ]

Calculated chemistry of [ 122-03-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 122-03-2 ]

Application In Synthesis of [ 122-03-2 ]

[ 122-03-2 ] Synthesis Path-Upstream 1~10

[ 122-03-2 ] Synthesis Path-Downstream 1~109

Technical Information

Related Functional Groups of [ 122-03-2 ]

Aryls

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 122-03-2 ]