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[ CAS No. 104-88-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 104-88-1
Chemical Structure| 104-88-1
Chemical Structure| 104-88-1
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Product Citations

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; chalcone ; drug likeliness properties ; imidazo[1,2-a]pyridine ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

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Product Details of [ 104-88-1 ]

CAS No. :104-88-1 MDL No. :MFCD00003379
Formula : C7H5ClO Boiling Point : -
Linear Structure Formula :(COH)C6H4(Cl) InChI Key :AVPYQKSLYISFPO-UHFFFAOYSA-N
M.W : 140.57 Pubchem ID :7726
Synonyms :

Calculated chemistry of [ 104-88-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.84
TPSA : 17.07 Ų

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) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.485 mg/ml ; 0.00345 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.15 mg/ml ; 0.00815 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.94
Solubility : 0.163 mg/ml ; 0.00116 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 104-88-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P273-P280-P302+P352+P312-P305+P351+P338+P310-P312-P362+P364-P391-P501 UN#:3077
Hazard Statements:H303-H312-H318-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 104-88-1 ]

* 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 [ 104-88-1 ]
  • Downstream synthetic route of [ 104-88-1 ]

[ 104-88-1 ] Synthesis Path-Upstream   1~109

  • 1
  • [ 104-88-1 ]
  • [ 80-73-9 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7705 - 7706
  • 2
  • [ 104-88-1 ]
  • [ 62882-02-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1959, vol. 89, p. 2222,2226
  • 3
  • [ 104-88-1 ]
  • [ 16687-61-9 ]
YieldReaction ConditionsOperation in experiment
66% With sodium azide; cerium(IV) tetraammonium sulfate dihydrate; hydroxylamine hydrochloride In N,N-dimethyl-formamide for 6 h; Reflux; Green chemistry General procedure: Aldehyde (1 mmol), hydroxylamine hydrochloride (2 mmol) and sodium azide (2 mmol) were added successively to a solution of (NH4)4Ce(SO4)4·2H2O (20 molpercent) in 5 mL DMF. The mixture was reflux for appropriate time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was treated with HCl (4N, 10  mL) and then the solution was poured into 100 mL water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ethyl acetate (75:25) as eluent to afford the pure solid tetrazole. All the products were characterized by 1H NMR, 13C NMR and HRMS.
Reference: [1] RSC Advances, 2016, vol. 6, # 94, p. 91999 - 92006
[2] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2116 - 2122
[3] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
[4] Synlett, 2012, vol. 23, # 20, p. 2927 - 2930
[5] Synthesis (Germany), 2013, vol. 45, # 4, p. 507 - 510
[6] Tetrahedron Letters, 2018, vol. 59, # 14, p. 1385 - 1389
[7] Synthetic Communications, 2011, vol. 41, # 14, p. 2081 - 2085
[8] Tetrahedron Letters, 2016, vol. 57, # 5, p. 523 - 524
[9] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29
[10] Synthetic Communications, 2017, vol. 47, # 7, p. 695 - 703
  • 4
  • [ 109-04-6 ]
  • [ 104-88-1 ]
  • [ 27652-89-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 43, p. 10681 - 10690
  • 5
  • [ 110-86-1 ]
  • [ 104-88-1 ]
  • [ 27652-89-7 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 21, p. 2124 - 2126
  • 6
  • [ 98-98-6 ]
  • [ 104-88-1 ]
  • [ 27652-89-7 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 14, p. 4156 - 4162
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 887,889
  • 7
  • [ 110-91-8 ]
  • [ 104-88-1 ]
  • [ 1204-86-0 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 99, p. 55815 - 55826
[2] Applied Organometallic Chemistry, 2018, vol. 32, # 1,
[3] Synthetic Communications, 2000, vol. 30, # 24, p. 4479 - 4488
  • 8
  • [ 104-88-1 ]
  • [ 27034-51-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1283 - 1292
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1760 - 1762
[3] Organic Letters, 2016, vol. 18, # 15, p. 3586 - 3589
  • 9
  • [ 87-41-2 ]
  • [ 104-88-1 ]
  • [ 53242-88-9 ]
YieldReaction ConditionsOperation in experiment
24.8%
Stage #1: With sodium hydroxide In methanol; ethyl acetate at 80℃;
Stage #2: at 80℃;
Isobenzofuran-l(3H)-one (0.50 g, 1.0 eq.) was dissolved in methanol (2.0 mL) and ethyl acetate (10.0 mL) and then 4-chlorobenzaldehyde (0.52 g, 1.0 eq.) was added thereto. NaOH (0.60 g, 4.0 eq.) was dissolved in methanol (8.0 mL) and added to the reaction solution. The mixture was then stirred overnight at 80°C. After confirming the disappearance of the starting material by TLC, the reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the obtained residue, and the extracted organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hydrazine hydrate (20.0 mL) was added to the obtained residue, followed by stirring overnight at 80°C. The reaction solution was cooled at room temperature and concentrated under reduced pressure. Ethanol (10.0 mL) was added to the obtained residue and cooled to 0°C using ice. After confirming that a transparent red solid was crystallized, it was filtered to obtain the desired intermediate 4- (4-chlorobenzyl)phthalazin-l(2H)-one (0.25 g, yield 24.8percent).
Reference: [1] Patent: WO2018/80216, 2018, A1, . Location in patent: Page/Page column 56-57
  • 10
  • [ 110-85-0 ]
  • [ 104-88-1 ]
  • [ 107785-63-7 ]
Reference: [1] Dalton Transactions, 2016, vol. 45, # 9, p. 3880 - 3887
[2] RSC Advances, 2015, vol. 5, # 115, p. 94768 - 94775
  • 11
  • [ 104-88-1 ]
  • [ 104-86-9 ]
  • [ 873-76-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 12, p. 2055 - 2058
[2] Tetrahedron, 2008, vol. 64, # 7, p. 1213 - 1217
  • 12
  • [ 104-88-1 ]
  • [ 104-86-9 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11493 - 11499
[2] Science, 2017, vol. 358, # 6361, p. 326 - 332
[3] Patent: EP2511283, 2012, A1,
[4] Organic and Biomolecular Chemistry, 2013, vol. 11, # 3, p. 407 - 411
[5] Patent: US2013/45942, 2013, A1,
[6] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
[7] RSC Advances, 2014, vol. 4, # 66, p. 34764 - 34767
[8] Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427
[9] Organic and Biomolecular Chemistry, 2016, vol. 14, # 45, p. 10599 - 10619
[10] Chemical Science, 2018, vol. 9, # 27, p. 5949 - 5956
[11] Patent: JP2015/172077, 2015, A,
  • 13
  • [ 540-69-2 ]
  • [ 104-88-1 ]
  • [ 104-86-9 ]
Reference: [1] Journal of the Karnatak University, 1957, vol. 2, p. 19,26
  • 14
  • [ 104-88-1 ]
  • [ 32863-33-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
  • 15
  • [ 288-32-4 ]
  • [ 104-88-1 ]
  • [ 10040-98-9 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 12, p. 8571 - 8578
[2] Synthetic Communications, 2008, vol. 38, # 4, p. 626 - 636
[3] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7951 - 7954
[4] Chemical Communications, 2004, # 7, p. 778 - 779
[5] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1938 - 1942
[6] Journal of the American Chemical Society, 2005, vol. 127, # 28, p. 9948 - 9949
[7] Tetrahedron, 2008, vol. 64, # 10, p. 2471 - 2479
[8] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4654 - 4660
  • 16
  • [ 288-32-4 ]
  • [ 104-88-1 ]
  • [ 67-68-5 ]
  • [ 25650-51-5 ]
  • [ 10040-98-9 ]
Reference: [1] Monatshefte fur Chemie, 2004, vol. 135, # 4, p. 419 - 423
  • 17
  • [ 104-88-1 ]
  • [ 536-40-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7525 - 7545
[2] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8846 - 8854
  • 18
  • [ 104-88-1 ]
  • [ 26385-24-0 ]
  • [ 3446-89-7 ]
Reference: [1] Patent: US2761873, 1953, ,
[2] Journal of medicinal chemistry, 1971, vol. 14, # 11, p. 1113 - 1115
  • 19
  • [ 2446-51-7 ]
  • [ 104-88-1 ]
  • [ 85-56-3 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 82, p. 9464 - 9466
  • 20
  • [ 141-97-9 ]
  • [ 104-88-1 ]
  • [ 57-13-6 ]
  • [ 5948-71-0 ]
YieldReaction ConditionsOperation in experiment
100% With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1 h; Microwave irradiation; Inert atmosphere General procedure: Aldehyde (1.0 mmol), ethyl acetoacetate (1.0 mmol), urea (1.5 mmol), Cu(OTf)2 (0.02 mmol), and EtOH (2 mL) were added to a microwave vial equipped with a magnetic stir bar. The reaction vessel was sealed and irradiated in a microwave reactor (CEM Discover.(TM). system) at a temperature of 100 °C for 1 h at a maximum power of 200 W. The reaction mixture was cooled to room temperature overnight and the resulting precipitate was filtered and washed with H2O and hexane. The identity and purity of the products were confirmed by TLC, high-resolution mass spectrometry, IR and 1H and 13C NMR spectroscopy
98% With bismuth vanadate In neat (no solvent) at 120℃; for 0.166667 h; Green chemistry General procedure: A mixture of the aldehyde, oxime and/or acylal (1 mmol),1,3-dicarbonyl compound (1 mmol), urea (or thiourea)(1.2 mmol) and BiVO4-NPs (30 mg, 9.3 molpercent) was heatedin an oil bath (120 °C) under solvent-free conditions. Aftercompletion of the reaction (monitored by TLC), the reactionmixture was cooled to room temperature and EtOH(5 mL) was added and filtered to separate the catalyst. Thenthe crude product was recrystallized from EtOH to give thepure product
97% With N-sulfonic acid poly(4-vinylpyridinium) chloride In neat (no solvent) at 100℃; for 0.0833333 h; General procedure: A mixture of the aldehyde (1 mmol), 1,3-dicarbonyl compound (1 mmol), urea (or thiourea) (1.2 mmol) and NSPVPC (20 mg) was heated in an oil-bath (100 °C) under solvent-free conditions. After completion of the reaction (monitored by TLC) the reaction mixture was cooled to room temperature, EtOH (5 mL) was added and filtered to separate the catalyst. Then the crude product was recrystallized from EtOH to give the pure product.
97% With Graphite In neat (no solvent) at 70℃; for 2 h; Green chemistry General procedure: A mixture of benzaldehyde (106mg, 1mmol), urea (60mg, 1mmol), ethylacetoacetate (130mg, 1mmol) and (10mg, 10percentw/w) graphite was heated at 70°C (120°C in case of thiourea). The heterogenous mixture slowly became clear and a solid product started to seperate out. After completion of the reaction (1h, TLC) the entire mass solidified. The solid mass was crushed, washed with 5mL of cold water to remove unreacted urea and filtered.The solid was then dissolved in hot ethanol, and the catalyst was separated by filtration. On cooling the filtrate pure crystals of the product (1a) was obtained, yield 97percent (237mg). In all the cases, the product obtained was characterized by comparing spectral data and melting points with literature data.
97% at 60℃; for 0.666667 h; General procedure: First, 2 mmol of aldehyde, 2mmol of ethyl acetoacetate, and 2 mmol of urea were stirred for 5 min at 60 C, and then the catalyst (0.1 g) was added, and stirring was continued at 60 C using a magnetic stirrer (Scheme 6) for an appropriate time (Table 4). After completion of the reaction (monitored by TLC), the product was extracted with ethyl acetate and filtered off using a vacuum pump. The product was obtained after removal of the solvent under reduced pressure and finally crystallized from ethanol.
97.59% With [Co(2,5-di(pyridin-4-yl)-1,3,4-oxadiazole)2(H2O)4](4-methylbenzenesulphonate)2(H2O)2 In neat (no solvent) at 80℃; for 2 h; Green chemistry General procedure: In the presence of a catalytic amount of MCCs (0.02mmol), a mixture of aldehyde (1mmol), ethyl acetoacetate (2mmol) and urea (1.5mmol) under solvent-free condition was heated 80°C in an oil bath for 2h. After the completion of the reaction, the reaction mixture was filtered and washed with cold water and methanol to afford the pure target product.
97% With 1,4-diazaniumbicyclo[2.2.2]octane diacetate In neat (no solvent) at 80℃; for 0.133333 h; Green chemistry General procedure: A mixture of aldehyde (1 mmol: 0.10 mL of aldehyde 1a, 0.14 g of aldehyde 1b, 0.12 g of aldehyde 1c, 0.13 g of aldehyde 1d, 0.15 g of aldehyde 1e, 0.15 g of aldehyde 1f, 0.17 g of aldehyde 1g, 0.12 g of aldehyde 1h, 0.18 g of aldehyde 1i, 0.15 g of aldehyde 1j, 0.12 g of aldehyde 1k, 0.08 mL of aldehyde 1l, 0.09 mL of aldehyde 1m, 0.07 mL of aldehyde 1n), ethyl acetoacetate (1 mmol), urea (1 mmol) or thiourea (1 mmol) and [DABCO] dihydroacetate (0.5 mmol) washeated at 80 °C for the required reaction time according to Table 1. After the completion of the reaction, as indicated by TLC, the reaction mixture was resolved in 20 mL of H2O. The product was separated by filtration and recrystallized from EtOH and dried to afford powdery compounds of 4a-q. The filtrate was concentrated under reduced pressure and washed with diethyl ether. Then, it was dried in a vacuum evaporator to recover the ionic liquid for subsequent use.
97% With yttrium(lll) nitrate hexahydrate In ethanol at 70℃; for 0.333333 h; Microwave irradiation General procedure: A mixture of ethylacetoacetate (1.54 mmol), aromatic or aliphatic aldehyde (1.54mmol), urea (1.84 mmol) and Y(NO3)3·6H2O (30.7 µmol) in 10mL Ethanol in a 100 mL round bottom flask fitted condenser was subjected to microwave heating at 70 °C for appropriatetime as mentioned in the Table-1. Then the reaction mixture was allowed to cool at room temperature and H2O (20 mL) was added.The precipitate appeared was collected by filtration and washedwith water. The solid obtained was further washed with n-Hexaneto remove excess aldehyde to get analytically pure product.
96% at 60℃; for 0.0333333 h; Microwave irradiation General procedure: A mixture of aldehyde (1.0 mmol), ethyl acetoacetate(1.0 mmol), urea (1.5 mmol), and nano-g-Fe2O3eSO3H was placedin a microwave reaction vial. The LG microwave oven MG 555f wasprogrammed to 250 W at 60 C. The progress of the reaction wasmonitored by TLC. After completion of the reaction, ethyl acetate(5 mL) was added and the catalyst was separated by applying anexternal magnet. The solvent was evaporated and the residue was recrystallized from EtOH/H2O to give a pure product, which gavesatisfactory spectroscopic data (1H NMR, 13C NMR, and IR) andmelting point, compared to data with those of samples synthesizedby reported procedures.
96% With N,N-diethyl-N-sulfoethanamminium hydrogen sulfate In neat (no solvent) at 70℃; for 0.25 h; Green chemistry General procedure: To a mixture of compounds consisting of arylaldehyde (1 mmol),β-ketoester (1 mmol) and urea (0.072 g, 1.2 mmol) or thiourea(0.091 g, 1.2 mmol) in a test tube, was added [Et3N–SO3H]HSO4(0.014 g, 0.05mmol). The resulting mixture was firstly stirred magneticallyat 70 °C, and after solidification of the reaction mixture, it wasstirred by a small rod at same temperature. After completion of thereaction, as monitored by TLC, the reaction mixture was cooled toroom temperature, and the resulting precipitate was recrystallizedfrom EtOH (95percent) to give the pure product.
96% With Fe+3-montmorillonite K10 In neat (no solvent) for 0.166667 h; Milling; Green chemistry General procedure: A mixture of aldehyde (1mmol), ethyl acetoacetate (1mmol), urea (1mmol) or thiourea (1mmol) and Fe+3-montmorillonite K10 (0.1 g) were added to a mortar and the mixture was pulverized with a pestle. A spontaneous reaction took place (Table 2, monitored every 20seconds by TLC EtOAc : petroleum ether 1:4 drops. After completion of reaction, as indicated by TLC, the reaction product was extracted by CHCl3/H2O. After evaporation of organicsolvent, the crude product was released and recrystallized from EtOH and dried to affordpowdery compounds of 4a-s. All of synthesized compound are known and were characterizedby IR, NMR and elemental analysis.
96% With sodium tosylate In water at 20℃; for 1.4 h; Green chemistry General procedure: A one-pot condensation of ethyl acetoacetate (1 mmol), aldehyde (1 mmol), and urea (1 mmol) was carried out by using a hydrotropic solution of NaPTS in a100 mL round-bottom flask containing 10 mL distilled water under normal temperature and pressure conditions. Ni-ZnO nanoparticles or ZnO nanoflakes (1 molpercent) were, respectively, used as a catalyst. The reaction mixture was stirred by using a magnetic stirrer under normal temperature and pressure conditions. The reaction was monitored by using the TLC technique (ethyl acetate:hexane 2:8, v/v). Ethyl acetate (15 mL) was added to the reaction mixture after completion of the reaction. Finally, the reaction mixture was centrifuged at 4000 rpm for 10 min. The catalyst settled at the bottom of the reaction mixture and the product was taken out of the pot. The catalyst was washed with deionized water and ethyl acetate and then dried in an oven at 120 °C before recycling. The procedure for the synthesis of DHPMs isshown in Fig. 1.
95% With gallium(III) triflate In neat (no solvent) at 90℃; for 0.5 h; Green chemistry General procedure: To a mixture of alkyl acetoacetate (or cycloketone) (1.0 mmol), aldehyde (1.0 mmol, for cycloketones: 2.0 mmol) and urea (or thiourea) (1.2 mmol), 0.1 equivalent Ga(OTf)3 was added. The mixture was stirred at 90 oC for appropriate time. After reaction completed by TLC analysis, water was added and the product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and evaporated. The residue was recrystallized from methanol or ethanol to obtain pure products.
95% With 1,3-disulfonic acid benzimidazolium chloride In neat (no solvent) at 80℃; for 0.116667 h; General procedure: In a 10-mL round-bottom flask equipped with a condenser, a mixture of the aromatic aldehyde (1 mmol), ethyl acetoacetate (1 mmol), urea or thiourea (1.5 mmol) and [Dsbim]Cl (0.0376 g, 10 molpercent) was stirred at 80°C, and the resulting mixture was kept under continuous stirring for lengths of time as specified in Table 3, with the progress of the reaction was followed by TLC. After completion of the reaction, the mixture was cooled to room temperature, and 3 mL of water was added. The ionicliquid was dissolved in water and filtered for separation of the crude product. The separated product was washed twice with water (2 9 3 mL). For recycling the catalysts, after the solid products were thoroughly washed with water, the water containing the ionic liquid (IL is soluble in water) was evaporated under reduced pressure, and the ionic liquid was recovered and reused. The solid product was purified by a recrystallization procedure in ethanol. All of the desired product(s) were characterized by comparison of their physical data with those of known compounds.
95% With Punica granatum peel In neat (no solvent) at 100℃; for 0.0833333 h; Green chemistry General procedure: To a mixture of benzaldehyde (1 mmol, 0.106 g), ethyl acetoacetate (1 mmol,0.130 g) and Punica granatum peel (0.03 g) at 100 °C, urea (1 mmol, 0.060 g) was added with stirring. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, cold distilled water (5 mL) was poured into the reaction flask, and the resultant mixture was decanted. The brown precipitate was dissolved in hot EtOH (3 mL) and the catalyst was separated by filtration. Then, the filtrate was distilled under reduced pressure and finally the crude product was recrystallized by EtOH to give the pure product (0.247 g, 95percent).
95% With silicon-supported ionic liquid catalyst In ethanol at 20 - 30℃; for 0.5 h; In a 25 mL round bottom flask, 4-chlorobenzaldehyde (0.140 g, 1 mmol) was added,Acetoacetate (0.130 g, 1 mmol), urea (0.060 g, 1 mmol),Catalyst (Si-IL) (0.0121 g, 10 molpercent) and 4 mL of absolute ethanol at room temperature,The reaction was carried out for 30 minutes under normal pressure, filtered and the ethanol was washed and the catalyst was recovered. The crude product obtained by removing the ethanol from the filtrate was recrystallized from 90percent ethanol (ethanol, volume ratio 9: 1) to obtain a pure product, Yield 95percent.
94% With bismuth (III) nitrate pentahydrate; silica gel In neat (no solvent) at 150℃; for 0.025 h; General procedure: A mixture of aldehyde (1 mmol), ethyl acetoacetate (1.1 mmol), urea or thiourea (1.1 mmol), was added to a round bottom flaskcontaining a mixture of silica gel (0.25 g) and catalyst (5 mole percent). The mixture was heated at 150 °C in oil bath for an appropriate duration of time (1-3 min). The completion of the reaction was confirmed by TLC. The same silica gel was loaded on a silica gel column and chromatographic separation using hexane-ethyl acetate furnished the products (4a-p).
94% With sulphated silica tungstic acid In neat (no solvent) at 70℃; for 0.166667 h; Green chemistry Aldehyde (3 mmol), ethyl acetoacetate or acetyl acetone (3.5 mmol), urea (4.5 mmol) and SSTA (200 mg) were mixed in a 25 mL round bottom flask for specified time (Table 4) at a temperature of 70 °C. The reaction mixture was cooled and added ethanol to solubilize the product. Catalyst was recovered by above-mentioned procedure. The filtrate was evaporated under reduced pressure to obtain the product. The compounds were recrystallized from ethanol.
94% With polyethylene supported Fe immobilization of alkyl imidazolium ionic liquid groups In neat (no solvent) at 80℃; for 1.83333 h; General procedure: For this, the PEt(at)Fe/IL catalyst (0.75 molpercent) was added to a homogeneous mixture of aldehyde (2 mmol), ethylacetoacetate (2 mmol) and urea (3 mmol). This was then magnetically stirred at 80 C while the reaction progress was monitored by thin layer chromatography (TLC). After completion of the process, hot ethanol (10 mL) was added to the reaction flask and the obtained solution was hotly filtered. The filtrate was then placed in an ice bath to precipitate crude crystals. These were recrystallized in ethanol to give pure Biginelli products in high to excellent yields. The products were characterized by IR, 1H-NMR, 13C-NMR and via comparison of their melting points with the reported ones.
94% With 20percent loaded [Dsim][CF3COO]/NaY composite In neat (no solvent) at 60℃; for 0.5 h; General procedure: A mixture of aromatic aldehyde (1 mmol), ethyl acetoacetate/acetophenone/cyclopentanone (1 mmol) and urea(1.5 mmol) was treated at 60 °C under neat condition (orsolvent-less grinding method using mortar and pestle atambient temperature) utilizing 3 mg of 20percent loaded [Dsim][CF3COO]/NaY composite for the appropriate time untilthe reaction was complete. The progress of the reactionwas monitored with thin layer chromatography in presenceof EtOAc and petroleum ether (1:2) as mobile phase. Themixture was diluted with hot ethanol (3 mL) to dissolvethe crude product. The catalyst was recovered as pure solidresidue after filtration of ethanol solution and then washedthree times with hot ethanol. The product was isolated assolid precipitate after addition of water to the ethanol solutionwith vigorous stirring. Recrystallization of the crudeproduct from saturated ethanol gave analytically pureproduct.
94% With 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate In acetonitrile for 0.333333 h; Reflux General procedure: A mixture of ethyl aceto-acetate(1.0 mmol) with aldehyde (1.0 mmol), urea (1 mmol), and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate(0.2 mmol) in acetonitrile was refluxed for20 min. Upon completion of the reaction water wasadded, and the solid product was filtered off, washe dwith ice-cold water, dried, and recrystalized from thanol.
94% at 100℃; for 0.583333 h; Green chemistry General procedure: A mixture of aromatic aldehyde (1.0 mmol), β-keto ester(1.0mmol), and urea (2mmol) was reacted at 100 °C usingthe n-Fe3O4(at)ZrO2/HPW (0.003 g, 15 molpercent) under solvent-free conditions for an appropriate time until the reactionwas completed. The reaction progress was monitoredby TLC [7:3 n-hexane: acetone]. After completion of thereaction, the mixture was diluted using hot ethanol and thereaction mixture was separated from the catalyst by meansof an external magnet. At last, the organic solvent wasevaporated under reduced pressure and the resulting solid crude product was then crystallized from hot ethanol toproduce the pure product.
94% With tris(pentafluorophenyl)borate In ethanol for 3 h; Reflux; Green chemistry General procedure: A mixture of benzaldehyde 1a (106 mg, 1 mmol), ethyl acetoacetate 2a (130 mg, 1 mmol) and urea 3a (90 mg,1.5 mmol) in EtOH (10 mL) was refluxed in the presence of B(C6F5)3 (18.1 mg, 1 molpercent). After completion of reaction, as indicated by TLC analysis, the solvent was evaporated. The resulting mass was treated with ice-cold water and the solid obtained was filtered, washed with cold water, dried and re-crystallized from ethanol to give pure product (4a).
94% With bis(p-sulfoanilino)triazine-functionalized silica-coated magnetite nanoparticles In neat (no solvent) at 100℃; for 0.75 h; General procedure: A mixture of aromatic aldehyde (1 mmol), b-keto ester or dimedone (1 mmol) and urea or thiourea (1.2 mmol) was stirred in presence MNPs-BSAT (20 mg) at 100 °C under solvent-free condition for the appropriate time (Scheme 1). After completion of the reaction as indicated by TLC (using n-hexane-ethyl acetate as eluent), the resulting mixture was diluted with hot ethanol (15 mL) and the catalyst separated by an external magnet and washed with hot ethanol (5 mL) two times. The filtrate was cooled to room temperature and the crude products which precipitated were collected and recrystallized from ethanol if necessary.

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  • 21
  • [ 141-97-9 ]
  • [ 104-88-1 ]
  • [ 17356-08-0 ]
  • [ 5948-71-0 ]
YieldReaction ConditionsOperation in experiment
85% With bismuth vanadate In neat (no solvent) at 120℃; for 1.5 h; Green chemistry General procedure: A mixture of the aldehyde, oxime and/or acylal (1 mmol),1,3-dicarbonyl compound (1 mmol), urea (or thiourea)(1.2 mmol) and BiVO4-NPs (30 mg, 9.3 molpercent) was heatedin an oil bath (120 °C) under solvent-free conditions. Aftercompletion of the reaction (monitored by TLC), the reactionmixture was cooled to room temperature and EtOH(5 mL) was added and filtered to separate the catalyst. Thenthe crude product was recrystallized from EtOH to give thepure product
Reference: [1] Journal of the Iranian Chemical Society, 2017, vol. 14, # 1, p. 75 - 87
  • 22
  • [ 141-97-9 ]
  • [ 104-88-1 ]
  • [ 57-13-6 ]
  • [ 5948-71-0 ]
YieldReaction ConditionsOperation in experiment
59% at 60℃; for 12 h; General procedure: To a mixture of aldehyde (2 mmol), ethyl acetoacetate (2 mmol), and either urea, thiourea or guanidine (2.5 mmol) was added ZnO (10 molpercent) or nanoZnO (5 molpercent) and the mixture was stirred at 60 °C under solvent-free conditions for the given times (Table 1). After the completion of the reaction (TLC monitoring), EtOAc (2× 10 mL) was added and the precipitated ZnO was filtered off. The resulting organic solution was washed with 10percent NaHCO3 and brine, dried over anhydrous Na2SO4, and evaporated to give the DHPM product. The products were structurally assigned by their IR, 1H NMR, 13C NMR spectra analysis and comparison to authentic samples.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 370, p. 117 - 122
  • 23
  • [ 21351-39-3 ]
  • [ 141-97-9 ]
  • [ 104-88-1 ]
  • [ 5948-71-0 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 5, p. 1177 - 1181
  • 24
  • [ 141-97-9 ]
  • [ 104-88-1 ]
  • [ 57-13-6 ]
  • [ 5948-71-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 2, p. 349 - 357
[2] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 2, p. 349 - 357
  • 25
  • [ 674-82-8 ]
  • [ 64-17-5 ]
  • [ 104-88-1 ]
  • [ 57-13-6 ]
  • [ 5948-71-0 ]
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 8, p. 930 - 932
[2] Synthesis, 2010, # 23, p. 4057 - 4060
  • 26
  • [ 104-88-1 ]
  • [ 74-89-5 ]
  • [ 104-11-0 ]
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[2] Journal of Antibiotics, 1998, vol. 51, # 1, p. 73 - 81
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 17, p. 2829 - 2837
  • 27
  • [ 104-88-1 ]
  • [ 104-11-0 ]
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[2] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
  • 28
  • [ 593-51-1 ]
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  • [ 104-11-0 ]
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  • 29
  • [ 15184-98-2 ]
  • [ 104-88-1 ]
  • [ 104-11-0 ]
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  • 30
  • [ 683-60-3 ]
  • [ 104-88-1 ]
  • [ 18962-05-5 ]
YieldReaction ConditionsOperation in experiment
75% With hemicucurbituril supported [Bmim]Cl In toluene for 10 h; Reflux General procedure: A mixture of aryl halide (1 mmol) and sodium alkoxide(3.0 mmol) was refluxed in the presence of 200 mg ofHmCucSILP catalyst in toluene (5 mL) for an appropriatetime as indicated in Table 2. After completion of thereaction, the reaction mixture was filtered and solvent wasevaporated in vacuo to give the crude product, which waspurified by column chromatography over silica gel usinghexane/EtOAc as the eluent.
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  • 31
  • [ 104-88-1 ]
  • [ 16588-34-4 ]
YieldReaction ConditionsOperation in experiment
97% for 2 h; Cooling To the mixture of nitrosonitric acid (55 mL) and sulfuric acid (55 mL) was added 4-chlorobenzaldehyde (70 g, 0.5 mol) in batches at 5 °C and stirred for 2 h.
Then the mixture was poured slowly to ice water (1 L) while stirring constantly.
The resulting precipitate was filtered and recrystallized from ethanol/water to give product 13 (90 g, 97percent) as white acicular crystal. Mp: 62-63 °C
94% at 0 - 20℃; for 0.5 h; Inert atmosphere General procedure: 10 mmol of the desired p-substituted benzaldehyde was dissolved in 5 mL of conc. sulfuric acid, and cooled to 0 °C, and then 1.2 equiv. of nitric acid was dissolved in 1 mL of conc. sulfuric acid, and then slowly added to the reaction mixture. The reaction was allowed to warmgradually to room temperature and stirred for 30 min at room temperature. It was then poured into 50 mL of ice-cold water. The produced precipitate was filtered and washed with cold water. The product was purified on reverse phase column chromatography with gradient increase of methanol in water containing 0.1percent of formic acid as eluent.
75% at 150℃; for 0.025 h; Microwave irradiation General procedure: The microwave (MW) reactor used was of CEM make, which was equipped with temperature, pressure, and MW power control units. An oven-dried MW vial was charged with a mixture containing aromatic compound, V2O5 (9 mg, 0.005 mmol) and 69percent HNO3 (0.063 mL, 1 mmol) and silica gel slurry, and irradiated in a MW (power input 140 W) at 150 °C for few minutes. After completion of the reaction, as as certained by TLC, the reaction mixture was treated with sodium bicarbonate; the organic layer was diluted with dichloromethane (DCM) and separated from aqueous layer. The crude product mixture was purified with ethyl acetate DCM mixture. The purity was checked with TLC. The products were identified by characteristic spectroscopic data.
70% at 0 - 40℃; for 1 h; General procedure: The nitration of aldehydes was carried out in a three-neckedflask of 50 ml with magnetic stirrer. H2SO4 25 ml (0.47 M)were cooled to 0 °C, 3.1 ml (0.070 M) of HNO3 were added,and then the aldehyde (0.06 M) was slowly added. Thereaction was carried out at a temperature of 0–5 °C. Then,the mixture was heated at 40 °C for 1 h. The reaction waspoured into ice water and filtered under a vacuum; thenitrobenzaldehydes were purified by recrystallization. Thescheme of reaction is showed in Fig. 1 (Furniss et al. 1989).The spectrums of 1H NMR of nitrobenzaldehydes wereobtained in CDCl3 and TMS as reference. 4-chloro-3-nitrobenzaldehyde: Yellow solid; mp 60–62 °C; yield: 70percent; 1H NMR (600MHz, CDCl3), 7.89(d, J = 8.16, 1H Ar–H), 8.25 (d, J = 8.16, 1H, Ar–H), 8.98(t, J = 8.16, 1H, Ar–H), 10.01 (s, 1H, –CHO).

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[16] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 3, p. 63
  • 32
  • [ 104-88-1 ]
  • [ 790-41-0 ]
YieldReaction ConditionsOperation in experiment
35% With tert.-butylhydroperoxide; copper dichloride In decane; acetonitrile at 80℃; for 5 h; General procedure: General procedure: The oxidative self-coupling reaction was carried out in atwo-necked round bottomed ask tted with a condenser under an airatmosphere. In a typical experiment, a mixture of aromatic aldehyde (1 mmol)and CuCl2 (13 mg, 10 mol percent) in MeCN (2 mL) was placed in the ask at roomtemperature. Then, TBHP (in decane (5-6 M), 1.5 equiv) was added to thereaction mixture slowly over a 5 min period, and the mixture was placed in anoil bath with magnetic stirring at 80 °C. After completion (TLC), the reactionmixture was cooled to room temperature and ethyl acetate (10 mL) andaqueous saturated NaHCO3 (10 mL) were added. The organic layer wascollected and dried with Na2SO4. The solvent was removed under reducedpressure. The residue was puried by column chromatography on silica gel(petroleum ether/ethyl acetate, 9:1) to afford the pure product.
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[2] Tetrahedron Letters, 2016, vol. 57, # 5, p. 566 - 569
[3] New Journal of Chemistry, 2017, vol. 41, # 3, p. 931 - 939
[4] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536
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  • [ 140-53-4 ]
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  • 35
  • [ 104-88-1 ]
  • [ 140-53-4 ]
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  • 36
  • [ 104-88-1 ]
  • [ 2420-26-0 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11735 - 11744
  • 37
  • [ 106-43-4 ]
  • [ 2420-26-0 ]
  • [ 5306-98-9 ]
  • [ 615-74-7 ]
  • [ 104-88-1 ]
  • [ 873-76-7 ]
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  • 38
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  • 39
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  • 40
  • [ 110-89-4 ]
  • [ 104-88-1 ]
  • [ 10338-57-5 ]
YieldReaction ConditionsOperation in experiment
83% With water; sodium t-butanolate In toluene at 105℃; for 5 h; Schlenk technique General procedure: An oven-dried Schlenk tube was charged with the aryl halide (2 mmol) and amine (2.5 mmol), FeOA–Pd (0.05 g, 0.04 mmol, 1.5 molpercent), base (3 mmol), solvent (5 mL) and additive. The resulting mixture was stirred for the appropriate time and temperature. After reaction completion the reaction mixture was then cooled to room temperature and the catalyst separated using a magnet, taken up in Et2O (4 mL), and washed with brine (5 mL). The resulting solution was dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel.
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  • 42
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  • [ 14548-38-0 ]
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[2] Letters in Drug Design and Discovery, 2014, vol. 11, # 5, p. 578 - 585
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  • [ 24091-92-7 ]
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  • [ 104-88-1 ]
  • [ 939-80-0 ]
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  • [ 35768-29-7 ]
  • [ 1187-46-8 ]
  • [ 104-88-1 ]
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  • 46
  • [ 558-13-4 ]
  • [ 541-41-3 ]
  • [ 104-88-1 ]
  • [ 20026-96-4 ]
Reference: [1] Journal of Chemical Research, 2018, vol. 42, # 4, p. 206 - 209
  • 47
  • [ 104-88-1 ]
  • [ 20026-96-4 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 100, p. 15864 - 15866
  • 48
  • [ 104-88-1 ]
  • [ 43141-66-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2001, vol. 111, # 2, p. 153 - 160
[2] Chemische Berichte, 1988, vol. 121, p. 1329 - 1340
[3] Synthesis, 1973, p. 787 - 789
[4] Patent: WO2009/121939, 2009, A2, . Location in patent: Page/Page column 58-59
  • 49
  • [ 104-88-1 ]
  • [ 536-74-3 ]
  • [ 57341-98-7 ]
YieldReaction ConditionsOperation in experiment
92% With nickel(II) ferrite; potassium carbonate In water at 100℃; for 3 h; General procedure: In a round-bottom flask equipped with a condenser for refluxingand a magnetic stirring bar, aryl/alkyl halide (1 mmol), phenylacetylene (1 mmol), K2CO3 (1.1 mmol), nickel ferrite nanoparticles(0.05 mmol) and water (3 ml) were added and heated at 100 °Cunder air atmosphere. The mixture was vigorously stirred underthese reaction conditions and its completion was monitored byTLC (EtOAc–n-hexane, 25:75).In each case, after completion of the reaction, the mixturewas dilutedwith diethyl ether and water. The organic layer was washed withbrine, dried over MgSO4, and concentrated under reduced pressureusing a rotary evaporator. The residue was purified by recrystallizationfrom ethanol and water.
91% With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide In N,N-dimethyl acetamide at 120℃; for 48 h; General procedure: Aryl halide and a terminal alkyne, with an equivalent molar ratioof 1.0–1.5, were added to a mixture of PdbisindoleSiO2Fe3O4(0.18 mmol, 20 mg) and DABCO (2.0 mmol, 224 mg) in a flask and2 mL DMA was added. The reaction mixture was stirred at 60C foraryl iodides and aryl bromides. The reaction temperature was setto 120C for aryl chlorides and 1 mmol TBAB was also added. Theprogress of the reaction was monitored by gas chromatography.After completion of the reaction, distilled water (2 mL) was addedto the reaction mixture and the crude product was extracted withethyl acetate (3 × 5.0 mL). The crude product was further purifiedby column chromatography using n-hexane and ethyl acetate as eluents.
80% With C59H51BrOP4Pd(2+)*3CF3O3S(1-); caesium carbonate In methanol at 60℃; for 24 h; General procedure: A mixture of an aryl halide (1 mmol), phenylacetylene (1.3 mmol), Cat. (0.001 molpercent), Cs2CO3 (2.5 mmol), and methanol (3 ml) was heated to 60 °C for 24 h. The reaction mixture was then cooled to room temperature and the solvent was removed under reduced pressure. The combined organic extracts were washed with brine and dried over CaCl2 and MgSO4. The solvent was evaporated and coupling product was obtained. The liquid residues were purified by silica gel column chromatography (n-hexane:EtOAc, 80:20) and the solid residues were purified by re-crystallization from ethanol and water.
78% With C37H29ClN3PPdS; triethylamine In N,N-dimethyl-formamide at 20℃; for 24 h; General procedure: In an oven-dried round bottom flask, a mixture of aryl halide (1 mmol), phenylacetylene (1.5 mmol), complex 1 (0.5 mol percent for aryl bromides, 1.0 mol percent for aryl chlorides) and Et3N (3.0 mmol) in DMF (5 mL) was taken. The reaction mixture was stirred at room temperature (12 h for aryl bromides, 24 h for aryl chlorides). At the end of the time period mentioned, the reaction mixture was diluted with EtOAc (20 mL) and washed with water (3 x 10 mL). The organic layer was dried over anhydrous Na2SO4, filtered and stripped off the solvent under reduced pressure. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixtures to afford the desired product in high purity. The products were characterized by 1H and 13C NMR analysis.
74% With [PdCl2((C6H5)2PCH2P(C6H5)2CHC(O)C6H4NO2)]; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 10 h; General procedure: A mixture of an aryl halide (1 mmol), phenylacetylene(1.3 mmol), catalyst (0.001 mol percent), K2CO3 (2.5 mmol), and DMF(2 ml) was heated to 130 C. The mixture was then cooled to roomtemperature and the solvent was removed under reduced pressure.The combined organic extracts were washed with brine and driedover CaCl2 or MgSO4. The solvent was evaporated and liquid residueswere purified by silica gel column chromatography (n-hexane:EtOAc, 80:20) and solid residues were purified byrecrystallization from EtOH and H2O. Products were identified bycomparison of their 1H and 13C NMR spectral data those reportedin the literature.
72% at 150℃; for 24 h; General procedure: To slurry of aryl halide (1 mmol), cuprous iodide (10 molpercent) andpalladium catalyst (a known molpercent) in an appropriate solvent(4 mL), phenylacetylene (1.2 mmol) and NaOH (1.7 mmol) wasadded and heated at required temp. After completion of the reaction(monitored by TLC), the flask was removed from the oil bathand water (20 mL) added, followed by extraction with ether(4 10 mL). The combined organic layers were washed with water(3 10 mL), dried over anhydrous Na2SO4, and filtered. Solventwas removed under vacuum. The residue was dissolved in hexaneand analyzed by GC–MS using Elite-5 columns, which are fused silicacapillary columns coated with 5percent diphenyl and 95percent dimethylpolysiloxane.
69% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16 h; Green chemistry General procedure: A mixture of aryl halide (1mmol), terminal alkyne (1mmol), K2CO3 (2mmol) and MNPFemTriazNHCAg complex (6) (100mg) in DMF (5mL) was stirred at 100°C. The progress of reaction was monitored by TLC. After completion, the reaction mixture was quenched in ice cold water and 6 was separated by external magnet. The reaction mixture was extracted with ethyl acetate (3×25mL). Evaporation of solvent in vaccuo followed by column chromatography over silica gel using petroleum ether/ethyl acetate afforded desired Sonogashira coupling products.
15 %Chromat. With copper(l) iodide; C18H14N2Pd; sodium hydroxide In ethanol; toluene at 25℃; for 24 h; General procedure: To slurry of aryl halide (1 mmol), cuprous iodide (10 molpercent) and palladium catalyst (a known molpercent) in 1:1 ethanol–toluene (4 mL), phenylacetylene (1.2 mmol) and NaOH (1.7 mmol) were added and heated at 25 °C. After completion of the reaction (monitored by TLC), the flask was removed from the oil bath and water (20 mL) added, followed by extraction with ether (4 × 10 mL). The combined organic layers were washed with water (3 × 10 mL), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC–MS.#10;

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[14] Tetrahedron Letters, 2006, vol. 47, # 18, p. 3023 - 3026
[15] Chemical Communications, 2002, # 8, p. 818 - 819
[16] New Journal of Chemistry, 2017, vol. 41, # 7, p. 2745 - 2755
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  • 50
  • [ 1719-19-3 ]
  • [ 104-88-1 ]
  • [ 57341-98-7 ]
YieldReaction ConditionsOperation in experiment
86% With tetrabutylammomium bromide; potassium carbonate; palladium dichloride; XPhos In water at 120℃; Inert atmosphere; Schlenk technique; Green chemistry General procedure: To a 25-mL Schlenk tube equipped with magnetic stir bar, aryl chloride (0.2 mmol), aryl propargylic alcohol (0.3 mmol), K2CO3 (2.0 equiv.), TBAB (1.0 equiv.), PdCl2 (2 molpercent), and Xphos (4 molpercent) were added in turn, then 2 mL H2O was added, and then the solution was refluxed for 24 h under N2 atmosphere. After the reaction was completed, the mixture was extracted with EtOAc or CH2Cl2. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to afford the desired product.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 10, p. 961 - 967
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Reference: [1] RSC Advances, 2016, vol. 6, # 76, p. 72810 - 72814
[2] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4543 - 4550
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  • [ 104-88-1 ]
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Reference: [1] Tetrahedron, 2007, vol. 63, # 39, p. 9741 - 9745
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Reference: [1] Patent: US2792418, 1954, ,
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 5733,5735
[3] Tetrahedron Asymmetry, 2005, vol. 16, # 14, p. 2475 - 2485
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 4, p. 845 - 849
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  • [ 35271-74-0 ]
Reference: [1] MedChemComm, 2015, vol. 6, # 4, p. 671 - 676
[2] Patent: CN106187794, 2016, A,
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  • [ 104-88-1 ]
  • [ 13726-16-4 ]
Reference: [1] Journal of the Indian Chemical Society, 2011, vol. 88, # 5, p. 727 - 730
  • 56
  • [ 104-88-1 ]
  • [ 4619-18-5 ]
Reference: [1] Patent: EP259085, 1988, A1,
  • 57
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  • [ 134-83-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 10, p. 2519 - 2525
  • 58
  • [ 104376-24-1 ]
  • [ 104-88-1 ]
  • [ 7295-50-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 48, p. 11465 - 11469
  • 59
  • [ 104-88-1 ]
  • [ 6212-33-5 ]
YieldReaction ConditionsOperation in experiment
34%
Stage #1: With water; ammonium chloride In methanol at 20℃; for 2 h;
Stage #2: With hydrogenchloride In water; toluene for 24 h; Reflux
A solution of 4-chlorobenzaldehyde (4.79 g, 34.08 mmol) inmethanol (10 mL) was added dropwise under vigorous stirring to a solution of KCN (2.48 g, 38.08 mmol) and NH4Cl (2.04 g,38.08 mmol) in water (10 mL). The reaction mixture was vigorously stirred at room temperature for 2 h. Then, water (25 mL) was added and the resulting mixture was extracted with toluene (25 mL). The aqueous layer was discarded and the toluene phase was extracted with 6N aqueous HCl (3 × 10 mL). The combined aqueous phasewas refluxed for 24 h. After that, the reaction mixture was evaporated and the resulting residue was suspended in water. The pHwas adjusted to 6–7 by means of the addition of small portions ofNa2CO3to precipitate the amino acid. The (4-chlorophenyl)glycinewas filtered and dried (2.16 g, 11.62 mmol, 34percent yield) and used inthe next step without further purification. Thionyl chloride (1.79 mL, 24.59 mmol) was added dropwiseto an ice-cooled suspension of (4-chlorophenyl)glycine (2.16 g,11.62 mmol) in dry methanol (29 mL). The resulting solution wasstirred at room temperature for 24 h. Then, the solvent was con-centrated under vacuum and the residue was lyophilized to afforda white solid (2.55 g, 10.80 mmol, 93percent yield). Mp 196–198C (lit.194–197C [10]);1H NMR (D2O, 400 MHz) (, ppm) 7.54–7.50 (m,2H, C6H4), 7.46–7.41 (m, 2H, C6H4), 5.30 (s, 1H, CH), 3.81 (s, 3H,CH3);13C NMR (D2O, 100 MHz) (, ppm) 169.2 (C), 135.9 (C), 129.7(2 x CH), 129.6 (2 x CH), 129.5 (C), 55.7 (CH3), 53.9 (CH); HRMS (ESI-TOF) calc. for [C9H11ClNO2]+requires 200.0473, found 200.0464.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2017, vol. 426, p. 407 - 418
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  • [ 104-88-1 ]
  • [ 6212-33-5 ]
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  • 61
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  • [ 67336-19-0 ]
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[2] Tetrahedron Letters, 1989, vol. 30, # 31, p. 4109 - 4110
  • 62
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  • [ 43189-37-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 17, p. 3327 - 3332
  • 63
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  • [ 104-88-1 ]
  • [ 67336-19-0 ]
  • [ 43189-37-3 ]
Reference: [1] Synthetic Communications, 1988, vol. 18, # 14, p. 1685 - 1690
  • 64
  • [ 67-56-1 ]
  • [ 104-88-1 ]
  • [ 10359-09-8 ]
  • [ 51513-29-2 ]
  • [ 2345-56-4 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 24, p. 4545 - 4556
  • 65
  • [ 104-88-1 ]
  • [ 411235-57-9 ]
  • [ 20034-50-8 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
  • 66
  • [ 141-82-2 ]
  • [ 104-88-1 ]
  • [ 19947-39-8 ]
YieldReaction ConditionsOperation in experiment
82.3% With ammonium acetate In ethanol at 75 - 80℃; for 8 h; To 25 mL of ethanol were added 5.00 g (35.6 mmol) of 4-chlorobenzaldehyde, 3.70 g (35.6 mmol) of malonic acid and 4.10 g (53.2 mmol) of ammonium acetate, and the mixture was reacted while stirring under reflux (75 to 80°C) for 8 hours. After completion of the reaction, the obtained reaction mixture was stirred at room temperature for 1 hour and then filtered to give 5.9 g of 3-amino-3-(4-chlorophenyl)propionic acid (racemic mixtures) (isolation yield based on 4-chlorobenzaldehyde: 82.3percent) as white powder. Incidentally, physical properties of the 3-amino-3-(4-chlorophenyl)propionic acid (racemic mixtures) were as follows. 1H-NMR (δ (ppm), D2O) : 2.93 (dd, 1H, J=17.1, 6.8Hz), 3.04 (dd, 1H, J=17.1, 7.8Hz), 4.63 (dd, 1H, J=7.8, 6.8Hz), 7.22 (s, 1H), 7.24 (s, 1H), 7.47 (s, 1H), 7.49 (s, 1H) 13C-NMR (δ (ppm), D2O) : 40.4, 53.9, 126.0, 131.9, 135.3, 137.1, 175.9 MS (EI) m/z: 199 (M+) MS (CI, i-C4H10) m/z: 200 (MH+)
75% With ammonium acetate In butan-1-olReflux General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.
Reference: [1] Patent: EP1621529, 2006, A1, . Location in patent: Page/Page column 31
[2] Preparative Biochemistry and Biotechnology, 2013, vol. 43, # 2, p. 207 - 216
[3] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1570 - 1576
[5] Heterocycles, 1989, vol. 28, # 2, p. 1015 - 1035
[6] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
[7] Journal of the American Chemical Society, 1946, vol. 68, p. 1137
[8] Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 5, p. 259 - 264
[9] Angewandte Chemie - International Edition, 2005, vol. 44, # 45, p. 7466 - 7469
[10] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1938 - 1950
[11] European Journal of Organic Chemistry, 2013, # 3, p. 557 - 565
[12] Bulletin of the Chemical Society of Japan, 2013, vol. 86, # 7, p. 870 - 879
[13] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1356 - 1365
  • 67
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  • 68
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  • [ 64473-35-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3549 - 3557
  • 69
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Reference: [1] Patent: CN106187794, 2016, A,
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  • 73
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  • [ 7099-88-9 ]
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  • 74
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  • [ 7424-00-2 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 41, p. 4255 - 4258
  • 75
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  • [ 87199-17-5 ]
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  • 76
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  • [ 43189-20-4 ]
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Reference: [1] Journal of the American Chemical Society, 1978, vol. 100, p. 8190 - 8202
  • 78
  • [ 1885-46-7 ]
  • [ 104-88-1 ]
  • [ 73960-07-3 ]
YieldReaction ConditionsOperation in experiment
49%
Stage #1: With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tert-butyl XPhos In 1,4-dioxane; water at 100℃; Inert atmosphere
Stage #2: With potassium hydroxide In 1,4-dioxane; water; acetonitrile at 20℃; for 0.0333333 h;
General procedure: [a] Reactions were performed on a 0.5 mmol scale to determine yields by 19F NMR spectroscopy with PI1CF3 as an internal standard added after the reaction.; Note: The hydroxylation reaction was set-up under an inert atmosphere according to the literature procedure. [Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.] To an oven-dried 4 mL vial was added Pd2(dba)3 (9.2 mg, .010 mmol, 4.0 mol percent Pd), 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (lBu- XPhos, 17.0 mg, .040 mmol, 8.0 mol percent), KOH (1.0-3.0 equiv), degassed H20 (150-300 μ) and dioxane (250-500 μΚ). The aryl halide (0.5 mmol, 1.0 equiv) was added (solid aryl halides were weighed into the vial prior to adding solvent, and liquid aryl bromides were added neat by syringe after the addition of solvent). The vial was sealed with a Teflon-lined cap and heated at 100 °C for 1-18 h. The solution was allowed to cool, and the reaction was diluted with acetonitrile (500-750 μ, such that the total volume of dioxane and acetonitrile is 1.0 mL) and 6M KOH (700-850 μ, such that the final aqueous solvent volume is 1.0 mL). The resulting mixture was stirred rapidly at room temperature, and HCF20Tf (210 μ, 1.5 mmol, 3.0 equiv) was added at once. Note: the reactions are exothermic. The mixture was stirred vigorously for 2 minutes. The reaction was diluted with ]0 (8 mL) and extracted with ether (2 x 8 mL). The combined organic layers were dried over MgS04, concentrated, and purified by silica gel chromatography.
Reference: [1] Patent: WO2014/107380, 2014, A1, . Location in patent: Paragraph 00166-00167
  • 79
  • [ 104-88-1 ]
  • [ 86212-34-2 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 120℃; for 3 h;
Stage #2: at 170℃; for 12 h;
General procedure: This is an adapted protocol for previous research carried out bydifferent authors.8 A suspension of a previously distilled benzaldehyde1a–h (50 mmol) and ammonium acetate (150 mmol) washeated at 120 C, and stirred for 3 h. After this time, the reactionwas cooled to room temperature, and the gummy residue waswashed with hexane. The resulting crude was basified with anaqueous 4 M NaOH solution (pH >10) and extracted with Et2O(4 20 mL). The organic phases were combined, dried, and filtered,and the solvent was evaporated under reduced pressure.Without further purification, the resulting intermediate was suspendedin an aqueous 50percent H2SO4 solution (40 mL), and the mixturewas heated overnight at 170 C. The reaction was then cooleddown in an ice-bath with stirring, and H2O (20 mL) was slowlyadded. The resulting solution was warmed until room temperatureand extracted with Et2O (4 60 mL). The aqueous phase was thenneutralized with a concentrated aqueous ammonia solution, andthen extracted with Et2O (4 60 mL). The organic phases werecombined, dried, and filtered, and the solvent was evaporated underreduced pressure, to give the corresponding meso-diamine 2a–h as a white, yellow, or brown solid (40–98percent isolated yield,Table 1).4.2.3
meso-1,2-Bis(4-chlorophenyl)-1,2-ethanediamine 2c
Yellow solid (3.43 g, 98percent isolated yield). Rf (60percent MeOH/EtOAc): 0.47; mp: 126-128 °C; IR (KBr): νmax/cm-1 3380, 2950, 1202, 1600, 980, and 820; δH (300.13 MHz, CDCl3, Me4Si): 1.53 (br s, 4H), 4.00 (s, 2H), 7.27-7.34 (m, 8H); δC (75.5 MHz, CDCl3, Me4Si): 62.0 (2CH), 128.5 (4CH), 128.9 (4CH), 133.4 (2C), 140.9 (2C); MS (ESI+, m/z): 281.0 [(M+H)+, 100percent]; HRMS (ESI+, m/z) calcd for C14H15Cl2N2 (M+H)+: 281.0607 found: 281.0592 (35Cl,35Cl), 283.0563 (35Cl,37Cl).
Reference: [1] Tetrahedron Asymmetry, 2014, vol. 25, # 4, p. 381 - 386
[2] Journal of the Chemical Society, 1957, p. 4407
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 18, p. 5454 - 5461
[4] Patent: US9988368, 2018, B1,
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 16, p. 7245 - 7260
[6] Patent: CN108610332, 2018, A,
  • 80
  • [ 104-88-1 ]
  • [ 276866-90-1 ]
YieldReaction ConditionsOperation in experiment
40% at 20℃; for 1.5 h; Iodines (1.12 g, 4.4 mmol), and sodium iodates (400mg, 2.2 mmol) are put into the reaction container in which the sulfuric acid (30 ml) is contained and it 30 min.is stirred in at a room temperature. Thereafter, 4- chlorobenzaldehydes (1.40 g, 10.0 mmol) are additionally put and it is stirred in at a room temperature for 1 hour.The reaction mixture is poured into the iced water after the reaction completion and the then generated solidis filtered and until the product is neutralized it washeswith water. After the solid filtered was melted in ethanol it recrystallized and intended compound 1.06 gs (4.00 mmol, 40percent) were obtained.
Reference: [1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 4, p. 951 - 956
[2] Tetrahedron, 2004, vol. 60, # 41, p. 9113 - 9119
[3] Synthesis, 2006, # 7, p. 1195 - 1199
[4] Patent: KR2016/149561, 2016, A, . Location in patent: Paragraph 0125; 0126; 0127
[5] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 180 - 190
  • 81
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  • [ 87661-20-9 ]
Reference: [1] Chemistry - A European Journal, 2002, vol. 8, # 18, p. 4234 - 4240
  • 82
  • [ 104-88-1 ]
  • [ 89-98-5 ]
  • [ 60767-69-3 ]
Reference: [1] Patent: DE98229, , ,
  • 83
  • [ 624-45-3 ]
  • [ 104-88-1 ]
  • [ 73257-49-5 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium acetate In neat (no solvent) at 55℃; for 3 h; Green chemistry General procedure: Polyhydroquinolines and DihydropyridinesA mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue
Reference: [1] Synlett, 2014, vol. 25, # 19, p. 2753 - 2756
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YieldReaction ConditionsOperation in experiment
96% With iron supported on copper/Zeolite Socony Mobil-5 nanocatalyst In water at 20℃; Sonication General procedure: In a typical experiment, aromatic aldehyde (1 mmol), bketoester(2 mmol), ammonium acetate (1 mmol), and Fe-Cu/ZSM-5 (3 wtpercent) in 2 ml water were introduced in a 20-mL heavy-walled pear-shaped two-necked flask with nonstandard-tapered outer joint. The flask was attached to a12-mm tip diameter probe, and the reaction mixture was sonicated at ambient temperature at 20 percent power of the processor. After completion of the reaction (monitored byTLC, within 5–8 min), the solid product was filtered,washed with water and ethanol, dried, and recrystallized from ethanol. The supported reagent was washed thrice with water and ethanol and dried under vacuum before reuse.
Reference: [1] Journal of the Iranian Chemical Society, 2016, vol. 13, # 2, p. 267 - 277
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YieldReaction ConditionsOperation in experiment
95% at 80℃; for 0.3 h; General procedure: A mixture of the alkyl or aryl aldehyde (1 mmol), -dicarbonyl(2 mmol) and ammonium acetate (1.5 mmol) in the presence ofFe3O4NPs (0.024 g, equal to 10 molpercent) was heated at 80C, withstirring. The progress of the reaction was monitored by TLC (elu-ent: EtOAc:n-hexane). After completion of the reaction, the mixturewas cooled to room temperature and then ethanol was added tothe resulting mixture and separated Fe3O4NPs by a normal mag-net. After evaporation of solvent, the solid product was filtered andrecrystallized from ethanol to give the pure products in 72–95percentyields based on the starting aldehyde.
95% With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10 h; In a 100 mL single-necked flask, 0.01 molpercent of Lewis acid-base bifunctional catalyst I was added (where Rf = CF3R1,R2, R3, R4, R5, R6 = F), 0.1 mol of p-chlorobenzaldehyde (R7 = 4-Cl-Ph), 0.1 mol of methyl acetoacetate (R8 = Me;Me), 0.1 mol of ammonium acetate, 10 mL of toluene, and the reaction was stirred at 100 ° C for 10 hours. TLC followed the reaction to complete the reaction. anti-The yield of the product II (R7 = 4-Cl-Ph; R8 = Me; R9 = Me) was 95percent; the catalyst system was reused 10 timesAfter its catalytic performance did not decline
94% for 2.25 h; Heating; Green chemistry General procedure: A mixture of aldehyde 1 (1 mmol), 1,3-dicarbonyl compound 2 (2 mmol), and nitrogen source 3 (3 mmol) were mixed and heated in the presence of a low-melting sugar mixture.The progress of the reaction was monitored by thin-layer chromatography (TLC) using n-hexane–ethyl acetate (7:3) as the solvent system. The Rf values of the product spots ranged from 0.5 to 0.6. After completion of the reaction, water was added to the reaction mixture to obtain the solid product as a precipitate. In cases where the product was obtained as a melt, several washings with water followed by bicarbonate solution gave crystalline products. The solids were filtered and washed with cold water. In most of the cases, the product obtained was pure, and when impure, the product was recrystallized from hot ethanol. Further two products were obtained as oils (Table 5, entries 4w and 4x). These products were extracted with ethyl acetate and dried over anhydrous Na2SO4. Evaporation of the solvent gave the pure product as an oil.
91% at 100℃; for 0.25 h; Green chemistry General procedure: To a glassy reactor equipped with a magnetic stir bar, amixture of aromatic aldehyde (1.0 mmol), β-keto ester(2 mmol), ammonium acetate (1.5 mmol) and n-Fe3O4(at)ZrO2/HPW (0.003 g, 15 mol percent) was added. The reactorwas put in an oil bath with the temperature of 100 °C andthe reaction was carried out under solvent-free condition.The progress of the reaction was monitored using TLCplates. When the reaction was completed, the mixture wasallowed to cool to room temperature. Afterwards, the mixturewas triturated with 5mL ethyl acetate and the catalystwas separated by the help of an external magnet. Then thesolvent was evaporated and the crude product was recrystallizedfrom EtOH/H2O to offer the pure product.
90% With uranyl nitrate hexahydrate; ammonium acetate In ethanol at 20℃; for 0.416667 h; Sonication General procedure: To a solution of aldehyde (1.0 mmol), ethyl/methyl acetoacetate/acetylacetone (2.0 mmol) and ammonium acetate (1.0 mmol) in ethanol (3 mL), uranyl nitrate (10 molpercent) was added and the resultant reaction mixture was sonicated at room temperature for the required time (Table 1). The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured into crushed ice. The obtained solid was filtered, washed thoroughly with water, dried, and purified by recrystallisation in ethanol.
84% at 55℃; for 3 h; Green chemistry General procedure: A mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue.
74% With C21H38N(1+)*Mo11O40PV(4-)*3H(1+); ammonium acetate In ethanol at 78℃; for 8 h; Green chemistry General procedure: The reaction was performed in a round bottom flask, whichwas equipped with a condenser and immersed in an oil bath. A mixture of methylacetoacetate (232 mg, 2 mmol), 2-nitrobenzaldehyde(151 mg, 1 mmol), ammonium acetate(100 mg, 1.3 mmol), and the selected catalyst (30 mg,1.5 percent mmol), in ethanol (8 mL) was thoroughly mixed andthen heated at 78 °C for 8 h. (to the end point of the reaction,checked by TLC). On cooling, the reaction mixture wasfiltered to separate the catalyst, the ethanol was evaporated,and the crude 1,4-dihydropyidine obtained was dried undervacuum (25 °C). The solid catalyst was washed with hexane(2 x 1 mL) and then, H2O (2 x 1 mL). The crude productwas recrystallized to give the pure 1,4-dihydropyridine.

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