[ CAS No. 39603-24-2 ] {[proInfo.proName]}

Name: 39603-24-2|5,7-Dimethylindoline-2,3-dione|97% HPLC
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SKU: A204326
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Quality Control of [ 39603-24-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 39603-24-2 ]

CAS No. :	39603-24-2	MDL No. :	MFCD00047219
Formula :	C₁₀H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFZSCCJTJGWTDZ-UHFFFAOYSA-N
M.W :	175.18	Pubchem ID :	38296
Synonyms :

Calculated chemistry of [ 39603-24-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.09
TPSA :	46.17 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) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	1.45
Log Po/w (WLOGP) :	0.87
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	2.44
Consensus Log Po/w :	1.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.18
Solubility :	1.15 mg/ml ; 0.00659 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	1.65 mg/ml ; 0.00943 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.55
Solubility :	0.0495 mg/ml ; 0.000282 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 39603-24-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 39603-24-2 ]

* 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 [ 39603-24-2 ]
Downstream synthetic route of [ 39603-24-2 ]

[ 39603-24-2 ] Synthesis Path-Upstream 1~9

1
[ 7343-12-6 ]
[ 39603-24-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sulfuric acid In water at 50 - 90℃; for 0.5 h;	General procedure: To a flask (100 mL) which contained concentrated sulfuricacid (20 mL) was added N-2-(hydroxyimino)acetamidederivatives (7.0 g) in portions at 50 °C with vigorous stirring.The reaction temperature was maintained at 50 °C-75 °Cduring the addition. After the addition was completed, themixture was heated to 80 °C and stirred for 30 min. The reactionmixture was cooled to room temperature and thenpoured onto ice (250 g). The solid which resulted was filteredout and dried over air to yield the crude which waspurified by dissolving in dilute sodium hydroxide (5percent, 100mL) followed by acidified with 4N hydrochloric acid (20mL). The solid which formed was filtered out and dried overair to provide the purified compounds 15a-g.

Reference： [1] Journal of Chemical Research, Miniprint, 1998, # 7, p. 1425 - 1434
[2] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498
[3] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[4] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488
[5] Gazzetta Chimica Italiana, 1955, vol. 85, p. 840,841
[6] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1955, vol. <8>18, p. 647,653
[7] Chemische Berichte, 1992, vol. 125, # 4, p. 849 - 856
[8] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11565 - 11572

2
[ 1421739-75-4 ]
[ 39603-24-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 80℃; for 0.666667 h; Cooling with ice	General procedure: A round-bottom flask is charged with concentrated sulfuric acid (33 ml) and is magnetically stirred at 50 °C open to the atmosphere. To the acid was added 2-[(benzyloxy)imino]-N-(4-n-hexylphenyl) (11 g, 32.5 mmole) in portions over 30 minutes. On completion of the addition the mixture was heated at 80 °C for an additional 10 minutes then allowed to cool to room temperature. The dark viscous solution was subsequently added in portions with rapid stirring to ice (750 ml). The crude product was isolated by vacuum filtration, and the filter cake washed with water. The crude product was dried under vacuum to give 6.3 g (85 percent) of an orange solid.#10;#10;

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 1008 - 1011

3
[ 4102-54-9 ]
[ 39603-24-2 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 3, p. 998 - 1003

4
[ 95-68-1 ]
[ 39603-24-2 ]

Reference： [1] Medicinal Chemistry, 2016, vol. 12, # 5, p. 489 - 498

5
[ 79-37-8 ]
[ 95-68-1 ]
[ 39603-24-2 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 646
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 647

6
[ 861586-96-1 ]
[ 64-17-5 ]
[ 39603-24-2 ]

Reference： [1] Chemische Berichte, 1922, vol. 55, p. 3182[2] Chemische Berichte, 1925, vol. 58, p. 686

7
[ 64-17-5 ]
[ 39603-24-2 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1918, vol. 166, p. 953[2] Annales de Chimie (Cachan, France), 1919, vol. <9> 11, p. 115

8
[ 64-19-7 ]
[ 39603-24-2 ]
[ 65-85-0 ]

Reference： [1] Chemische Berichte, 1923, vol. 56, p. 2117

9
[ 39603-24-2 ]
[ 14438-32-5 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1929, p. 583
[2] Journal of the American Chemical Society, 1965, vol. 87, # 24, p. 5554 - 5558
[3] Chemische Berichte, 1992, vol. 125, # 4, p. 849 - 856
[4] Chemistry - A European Journal, 2008, vol. 14, # 36, p. 11565 - 11572

[ 39603-24-2 ] Synthesis Path-Downstream 1~73

1
[ 39603-24-2 ]
[ 26673-32-5 ]
[ 672287-53-5 ]

Reference： [1]Journal of the Chemical Society,1952,p. 279

2
[ 39603-24-2 ]
[ 4225-92-7 ]
3-hydroxy-2-mesityl-6,8-dimethyl-quinoline-4-carboxylic acid [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1932,vol. <2> 133,p. 259,268

3
[ 39603-24-2 ]
[ 95-54-5 ]
7,9-dimethyl-6<i>H</i>-indolo[2,3-<i>b</i>]quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20℃; for 0.233333h;Green chemistry;	General procedure: A mixture of aromatic diamine derivatives (2 mmol) and a 1,2-dicarbonyl compound (2 mmol) in ionic liquid (2 mL) was stirred atroom temperature for the appropriate time. The progress of the reaction was monitored by TLC (n-Hexane: EtOAc, 7:3), after completion of the reaction, the reaction mixture was diluted with water and extracted using diethyl ether (30 ml). The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford the corresponding product. The residual ionic liquid was dried under vacuum and reused. The same procedure was repeated for the reaction of aromatic anilines with isatin and acenaphthoquinone and phenaacylbromide. All the products obtained were characetrised by IR,1HNMR, 13CNMR and Mass studies.
91%	In ethylene glycol; at 80℃; for 0.233333h;Microwave irradiation; Green chemistry;	General procedure: Indole-2,3-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol) and 5 mol% of Cu doped CdS NPs in ethylene glycol (10 ml) was introduced in a 50 ml round-bottomed flask. The flask was placed in the microwave cavity and subjected to irradiation for appropriate time at 80 C using a maximum power of 300 W. When the reaction was complete, the reaction mixture was extracted with ethylacetate; the organic layer was removed under reduced pressure to afford the crude product. The pure products were obtained by crystallization from ethanol.
91%	With aminosulfonic acid; In ethanol; at 20℃; for 1.5h;	General procedure: To a 25 ml round bottom flask, a mixture of isatin / acenaphthoquinone / 2-hydroxynaphthoquinone/ ninhydrin (1 mmol), o-phenylene diamine (1 mmol) in ethanol (95 %, 10 mL) and sulfamic acid (20 mol %) was added. The reaction mixture was stirred at ambient temperature for time mentioned in Table II, monitored by TLC. After completion of reaction, the mixture was filtered washed with ethanol and dried to furnish the desired pure products in high yields.

Reference： [1]Journal of Molecular Structure,2019,vol. 1198
[2]Journal of Molecular Catalysis A: Chemical,2014,vol. 394,p. 244 - 252
[3]Synthetic Communications,2014,vol. 44,p. 3384 - 3391
[4]Bulletin de la Societe Chimique de France,1946,p. 586,587

5
[ 39603-24-2 ]
[ 14438-32-5 ]

Reference： [1]Archiv der Pharmazie,1929,p. 583
[2]Journal of the American Chemical Society,1965,vol. 87,p. 5554 - 5558
[3]Chemische Berichte,1992,vol. 125,p. 849 - 856
[4]Chemistry - A European Journal,2008,vol. 14,p. 11565 - 11572

6
[ 7343-12-6 ]
[ 39603-24-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sulfuric acid; In water; at 50 - 90℃; for 0.5h;	General procedure: To a flask (100 mL) which contained concentrated sulfuricacid (20 mL) was added N-2-(hydroxyimino)acetamidederivatives (7.0 g) in portions at 50 C with vigorous stirring.The reaction temperature was maintained at 50 C-75 Cduring the addition. After the addition was completed, themixture was heated to 80 C and stirred for 30 min. The reactionmixture was cooled to room temperature and thenpoured onto ice (250 g). The solid which resulted was filteredout and dried over air to yield the crude which waspurified by dissolving in dilute sodium hydroxide (5%, 100mL) followed by acidified with 4N hydrochloric acid (20mL). The solid which formed was filtered out and dried overair to provide the purified compounds 15a-g.

Reference： [1]Journal of Chemical Research, Miniprint,1998,p. 1425 - 1434
[2]Medicinal Chemistry,2016,vol. 12,p. 489 - 498
[3]Journal of Organic Chemistry,1952,vol. 17,p. 149,153
[4]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1955,vol. <8>18,p. 647,653
[5]Chemische Berichte,1992,vol. 125,p. 849 - 856
[6]Chemistry - A European Journal,2008,vol. 14,p. 11565 - 11572

7
[ 39603-24-2 ]
[ 54020-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	With borane-THF; In tetrahydrofuran; at 0 - 20℃;	45. A. SYNTHESIS OF 5, 7-DIFNETHYL-IH-INDOLE To solution of 5, 7-dimethyl-lH-indole-2, 3-dione in tetrahydrofuran at 0 C was added 1. 0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (40 mL). After stirred at room temperature overnight, a 5% HCl solution was added to the mixture and it was stirred 20 minutes. It was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. Extracts were dried over magnesium sulfate and evaporated to dryness to afford the title compound as oil.

Reference： [1]Patent: WO2005/33112,2005,A2 .Location in patent: Page/Page column 97

8
[ 1122-54-9 ]
[ 39603-24-2 ]
[ 436092-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol at 80℃;

Reference： [1]Location in patent: experimental part Peng, Chi-Chi; Cape, Jonathan L.; Rushmore, Tom; Crouch, Gregory J.; Jones, Jeffrey P. [Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8000 - 8011]

9
[ 350-03-8 ]
[ 39603-24-2 ]
[ 587851-87-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol at 80℃;

10
[ 39603-24-2 ]
[ 1118-61-2 ]
[ 371-14-2 ]
[ 1308671-50-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With indium(III) chloride; In water; at 100℃; for 0.166667h;	General procedure: A mixture of phenylhydrazine (1 mmol), 3-aminocrotononitrile (1 mmol), and InCl3 (0.1 mmol) in water (10 ml) was added to isatin (1 mmol) and the reaction mixture heated under reflux at 100 C for 10 min. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature; the precipitate was filtered off and washed with methanol to obtain pure 13 as a colorless solid. Spectroscopic data for all the compounds are given below.

Reference： [1]Tetrahedron,2011,vol. 67,p. 3201 - 3208

11
[ 39603-24-2 ]
[ 1118-61-2 ]
[ 100-63-0 ]
[ 1308671-46-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With indium(III) chloride; In water; at 100℃; for 0.166667h;	General procedure: A mixture of phenylhydrazine (1 mmol), 3-aminocrotononitrile (1 mmol), and InCl3 (0.1 mmol) in water (10 ml) was added to isatin (1 mmol) and the reaction mixture heated under reflux at 100 C for 10 min. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature; the precipitate was filtered off and washed with methanol to obtain pure 13 as a colorless solid. Spectroscopic data for all the compounds are given below.

Reference： [1]Tetrahedron,2011,vol. 67,p. 3201 - 3208

12
[ 39603-24-2 ]
[ 126-81-8 ]
[ 109-77-3 ]
[ 1321787-76-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium acetate; In neat (no solvent); at 25℃; for 0.25h;Green chemistry;	General procedure: Isatin 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

Reference： [1]Synthetic Communications,2011,vol. 41,p. 2905 - 2919
[2]Green Chemistry,2011,vol. 13,p. 2135 - 2145
[3]Canadian Journal of Chemistry,2017,vol. 95,p. 194 - 198
[4]Monatshefte fur Chemie,2016,vol. 147,p. 755 - 760
[5]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 61 - 65

13
[ 39603-24-2 ]
[ 100-39-0 ]
[ 1017609-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; for 24h;Reflux;	General procedure: To a mixture of the protecting reagent RBr (0.2 mmol) and K2CO3 (0.138 g) in MeCN (10 mL), isatin (6) was added (0.147 g) at room temperature. After that, the reaction mixture was stirred 24 h at reflux. Then, the solvent was evaporated under vacuum, and the reaction crude was purified by column chromatography (SiO2, Hex:EtOAc 8:2), giving rise to the corresponding product 7.

Reference： [1]Chemical Communications,2012,vol. 48,p. 3336 - 3338
[2]Synlett,2011,p. 2256 - 2258
[3]Chemistry - A European Journal,2012,vol. 18,p. 9645 - 9650
[4]Synlett,2012,vol. 23,p. 2274 - 2278
[5]Molecules,2015,vol. 20,p. 15807 - 15826
[6]Organic Letters,2019,vol. 21,p. 9742 - 9746

14
[ 39603-24-2 ]
[ 762-72-1 ]
[ 1309578-01-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6398 - 6401

15
[ 39603-24-2 ]
[ 75-07-0 ]
C₁₂H₁₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 9-epi-9-amino-9-deoxyquinine; water; benzoic acid; In tetrahydrofuran; at 5℃; for 12h;	General procedure: To a mixture of isatin 1a (14.7 mg, 0.1 mmol), H2O (5.4 muL, 0.3 mmol), quinine-derived amine 3 (3.3 mg, 0.01 mmol), and benzoic acid (3.66 mg, 0.03 mmol) in THF (1.0 mL) at 5 C was added acetaldehyde (22.0 mg, 0.5 mmol). After the reaction mixture was stirred for 15 h at this temperature, it was cooled to 0 C. Methanol (2 mL) and NaBH4 (20.0 mg, 0.5 mmol) were then added sequentially. The resulting reaction mixture was stirred for an additional 30 min at 0 C. Water (5.0 mL) was added to quench the reaction. The reaction mixture was extracted with ethyl acetate (10 mL x 3). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2 to 2:1) to give the pure product 2a.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 1768 - 1771

16
[ 67-52-7 ]
[ 39603-24-2 ]
[ 126-81-8 ]
[ 1374301-16-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With nano structured silica bonded 1,4-diaza-bicyclo[2.2.2]octane sulfonic acid chloride; In water; for 1.5h;Reflux;	General procedure: A mixture of isatin derivatives or acenaphthenquinone(1 mmol), barbituric acid (1 mmol), 1, 3-dicarbonyl compounds(1 mmol), SBDBSAC (0.02 g) and H2O (5 mL) was added to a in a25 mL round-bottomed flask connected to a reflux condenser, andstirred under reflux conditions. After completion of the reaction, asmonitored by TLC, the reaction mixture was cooled to room temper-ature. Methanol (20 mL) was added, stirred and refluxed for 3 min.Then, the resulting mixture was centrifuged for the separation of the catalyst from the product and remaining starting materials.After the separation of catalyst from the reaction mixture, methanolwas removed and the solid residue (crude product) was trituratedby a mixture of ethanol and water (9/1) to give the pure product.

Reference： [1]ACS Combinatorial Science,2012,vol. 14,p. 335 - 341
[2]Journal of Molecular Catalysis A: Chemical,2016,vol. 420,p. 246 - 253

17
[ 14678-02-5 ]
[ 67-52-7 ]
[ 39603-24-2 ]
[ 1397289-51-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	With toluene-4-sulfonic acid; In water; at 70℃; for 24h;	General procedure: A solution of isatin (1 mmol), barbituric acid (1 mmol), 3-amino-5-methyl isoxazole (1 mmol), and p-TsOH (0.2 mmol) in water (10 mL) was stirred for 24 h at 70 C in oil bath. After completion of the reaction, which was followed by TLC (n-hexane/EtOAc), the warm reaction mixture was filtered. The residue was washed with water and then recrystallized from ethanol to give the pure product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 8472 - 8479

18
[ 39603-24-2 ]
[ 51-35-4 ]
[ 16176-38-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With cetyltrimethylammonim bromide; In water; at 80℃; for 0.5h;Green chemistry;	General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 1629 - 1634
[2]Journal of Chemical Research,2012,vol. 36,p. 581 - 583,3

19
[ 1421739-75-4 ]
[ 39603-24-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sulfuric acid; at 80℃; for 0.666667h;Cooling with ice;	General procedure: A round-bottom flask is charged with concentrated sulfuric acid (33 ml) and is magnetically stirred at 50 C open to the atmosphere. To the acid was added 2-[(benzyloxy)imino]-N-(4-n-hexylphenyl) (11 g, 32.5 mmole) in portions over 30 minutes. On completion of the addition the mixture was heated at 80 C for an additional 10 minutes then allowed to cool to room temperature. The dark viscous solution was subsequently added in portions with rapid stirring to ice (750 ml). The crude product was isolated by vacuum filtration, and the filter cake washed with water. The crude product was dried under vacuum to give 6.3 g (85 %) of an orange solid.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1008 - 1011

20
[ 39603-24-2 ]
[ 17136-36-6 ]
andrographolide [ No CAS ]
[ 1415404-83-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	In methanol at 100℃; for 0.333333h; Microwave irradiation; Green chemistry; stereoselective reaction;
	for 0.25h; Microwave irradiation;

Reference： [1]Hazra, Abhijit; Bharitkar, Yogesh P.; Chakraborty, Debanjana; Mondal, Susanta Kumar; Singal, Nupur; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Banerjee, Sukdeb; Mondal, Nirup B. [ACS Combinatorial Science, 2013, vol. 15, # 1, p. 41 - 48]
[2]Chakraborty, Debanjana; Maity, Arindam; Jain, Chetan K.; Hazra, Abhijit; Bharitkar, Yogesh P.; Jha, Tarun; Majumder, Hemanta K.; Roychoudhury, Susanta; Mondal, Nirup B. [MedChemComm, 2015, vol. 6, # 4, p. 702 - 707]

21
[ 39603-24-2 ]
[ 1660-94-2 ]
C₁₅H₂₀NO₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 0℃;	General procedure: To a stirred solution of tetraethyl methylenebis(phosphonate) (0.69 mmol, 200 mg) in anhydrousTHF (10 mL) was added NaH (1.52 mmol, 60 mg) slowly at 0 C. After 10 minutes, a solution ofisatine (0.69 mmol) in anhydrous THF (2 mL) was added. After completion (monitored by TLC),water was added, and the mixture was extracted with ethyl acetate (3 × 20 mL). The combinedorganic phases were dried with anhydrous Na2SO4 and concentrated under reduced pressure. Theresidue was purified by flash chromatography on silica gel (hexane/ethyl acetate). To a stirredsolution of the above product (0.65 mmol, 182 mg) in anhydrous THF (10 mL) was added DMAP(0.13 mmol) and TEA (0.98 mmol) at 0 C. Then (Boc)2O (0.78 mmol, 170 mg) was added. Aftercompletion, water was added, and the mixture was extracted with ethyl acetate (3 × 20 mL). Thecombined organic phases were dried with anhydrous Na2SO4 and concentrated under reducedpressure. The residue was purified by flash chromatography on silica gel (hexane/ethyl acetate).

Reference： [1]Tetrahedron,2013,vol. 69,p. 10369 - 10374

22
[ 16312-21-3 ]
[ 39603-24-2 ]
5-(3-hydroxy-5,7-dimethyl-2-oxoindolin-3-yl)-3-methylthiazolidine-2,4-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 1473 - 1480

23
[ 39603-24-2 ]
[ 91-59-8 ]
[ 762-21-0 ]
[ 1564285-72-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With antimony(III) chloride; In acetonitrile; at 80℃; for 8h;Inert atmosphere;	General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).
78%	With antimony(III) chloride; In acetonitrile; at 80℃; for 8h;Inert atmosphere;	General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1370 - 1372
[2]Tetrahedron Letters,2014,vol. 55,p. 1370 - 1372

24
[ 39603-24-2 ]
[ 91-59-8 ]
[ 762-42-5 ]
[ 1564285-69-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With antimony(III) chloride; In acetonitrile; at 80℃; for 8h;Inert atmosphere;	General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).
81%	With antimony(III) chloride; In acetonitrile; at 80℃; for 8h;Inert atmosphere;	General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 1370 - 1372
[2]Tetrahedron Letters,2014,vol. 55,p. 1370 - 1372

25
[ 606-23-5 ]
[ 39603-24-2 ]
[ 134-32-7 ]
5',7'-dimethylspiro[benzo[h]indeno [1,2-b]quinoline-7,3'-indoline]-2',8(13H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With acetic acid; at 80℃; for 24h;	General procedure: A solution of an isatin (3) (1 mmol), a C-H acidderivative (2) (1 mmol), and naphthalen-1-amine (1)(1 mmol) was heated at 80 C in acetic acid (5 mL)for 24 h. After completion of the reaction as indicatedby TLC (MeOH/AcOEt, 1:4), the residue wasfiltered and washed successively with gl. acetic acid andCHCl3 (3 × 10 ml). The crude product thus obtainedwas crystallized from MeOH or EtOH and dried atroom temperature. The final product was obtained as a powder.

Reference： [1]Journal of Chemical Sciences,2014,vol. 126,p. 169 - 176
[2]Journal of Chemical Sciences,2014,vol. 126,p. 169 - 176

26
[ 61550-02-5 ]
[ 39603-24-2 ]
3-(2,5-dihydro-5-oxofuran-2-yl)-3-hydroxy-5,7-dimethylindolin-2-one [ No CAS ]
3-(2,5-dihydro-5-oxofuran-2-yl)-3-hydroxy-5,7-dimethylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of isatin 1 (0.5 mmol) in THF (2 mL) was added quinine (0.017 g, 10 mol%). The mixture was cooled to -78 C and stirred at this temperature for 15 minutes. Then the solution of 2-(trimethylsilyloxy)furan 2 (0.156 g, 1 mmol) in THF (1 mL) was added dropwise. The mixture was stirred at -78 C for 15 minutes. The reaction was monitored by TLC. After the completion ofthe reaction it was quenched by addition of 10% aqueous HCl (2.0 mL) and the mixture wasextracted with ethyl acetate (3×5 mL). The combined organic layer was washed with brine solution,dried over MgSO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (AcOEt/hexane) to afford the product as a white solid.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 936 - 942

27
[ 501-30-4 ]
[ 39603-24-2 ]
[ 105-56-6 ]
[ 1581291-29-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,4-diaza-bicyclo[2.2.2]octane; In methanol; for 12h;Reflux;	General procedure: A solution of an isatin or 9,10-Phenanthrenequinone (1mmol), koijc acid (1 mmol), malononitrile or ethyl and/or methyl cyanoacetate (1 mmol) and DABCO (20 mol %) in MeOH (5 ml) was stirred for 12 h under reflux in oil bath. After completion of the reactions, which has been followed by TLC (EtOAc:n-hexane, 5:1), the reaction mixture was remained for 12 h at room temperature to get white and pure crystals.

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2014,vol. 17,p. 132 - 140

28
[ 120-72-9 ]
[ 39603-24-2 ]
[ 694525-96-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 0.25h;	General procedure: A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol %), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.

Reference： [1]Synthetic Communications,2014,vol. 44,p. 2029 - 2036

29
[ 39603-24-2 ]
[ 882-36-0 ]
[ 1608483-78-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1-butyl-3-methylimidazolium Tetrafluoroborate In toluene at 100℃; for 0.666667h; Inert atmosphere; Combinatorial reaction / High throughput screening (HTS); Microwave irradiation; Green chemistry;

Reference： [1]Xia, Likai; Idhayadhulla, Akber; Lee, Yong Rok; Kim, Sung Hong; Wee, Young-Jung [ACS Combinatorial Science, 2014, vol. 16, # 7, p. 333 - 341]

30
[ 39603-24-2 ]
[ 79-19-6 ]
[ 1526924-25-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	In glycerol; at 40℃; for 3h;Green chemistry;	General procedure: To a round bottom flask containing 5 ml glycerol was added respective isatin (1 mmol) and respective thiosemicarbazide/semicarbazide (1 mmol) under stirring. The temperature of the reaction was set at 40 oC and the resulting mixture was stirred till completion and progress of reaction was monitored with TLC (Hexane/EtOAc 2:1). The reaction was quenched with hot water whence glycerol got dissolved in water and the resulting insoluble solid precipitate was filtered and dried to obtain the crude product which was as good as pure (1H NMR). The aqueous phase containing glycerol was extracted with methyl t-butyl ether (4 × 25 mL) to remove any trace of organic compounds and then evaporated in vacuo to give pure glycerol which was used for the next cycle.
82%	With C10H16NO4S(1+)*HO4S(1-); In water; at 20℃; for 0.2h;Green chemistry;	General procedure: A mixture of isatin (1 mmol), thiosemicarbazide/4-methyl-3-thiosemicarbazide (1 mmol) was taken in 5 cm3 watercontaining 20 mol% of [2-HMPyBSA]HSO4 and stirred atroom temperature for the time specified in Table 2. Theprogress of reaction was monitored by TLC. After completionof the reaction, the reaction mixture was filteredand washed with ethanol to yield corresponding product inpure form. Products were characterized by usual spectraltechniques. (i.e. IR, 1H, 13C NMR, and MS).

Reference： [1]Synthetic Communications,2017,vol. 47,p. 1999 - 2006
[2]RSC Advances,2013,vol. 3,p. 25723 - 25726
[3]Monatshefte fur Chemie,2016,vol. 147,p. 2143 - 2149

31
[ 39603-24-2 ]
[ 4426-72-6 ]
[ 1526924-18-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	In glycerol; at 40℃; for 3h;Green chemistry;	General procedure: To a round bottom flask containing 5 ml glycerol was added respective isatin (1 mmol) and respective thiosemicarbazide/semicarbazide (1 mmol) under stirring. The temperature of the reaction was set at 40 oC and the resulting mixture was stirred till completion and progress of reaction was monitored with TLC (Hexane/EtOAc 2:1). The reaction was quenched with hot water whence glycerol got dissolved in water and the resulting insoluble solid precipitate was filtered and dried to obtain the crude product which was as good as pure (1H NMR). The aqueous phase containing glycerol was extracted with methyl t-butyl ether (4 × 25 mL) to remove any trace of organic compounds and then evaporated in vacuo to give pure glycerol which was used for the next cycle.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 1999 - 2006
[2]RSC Advances,2013,vol. 3,p. 25723 - 25726

32
[ 452-58-4 ]
[ 39603-24-2 ]
[ 96248-21-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethylene glycol; at 80℃; for 0.233333h;Microwave irradiation; Green chemistry;	General procedure: Indole-2,3-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol) and 5 mol% of Cu doped CdS NPs in ethylene glycol (10 ml) was introduced in a 50 ml round-bottomed flask. The flask was placed in the microwave cavity and subjected to irradiation for appropriate time at 80 C using a maximum power of 300 W. When the reaction was complete, the reaction mixture was extracted with ethylacetate; the organic layer was removed under reduced pressure to afford the crude product. The pure products were obtained by crystallization from ethanol.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2014,vol. 394,p. 244 - 252

33
[ 39603-24-2 ]
[ 1896-62-4 ]
5,7-dimethyl-6'-phenyl-5',6'-dihydrospiro[indoline-3,2'-pyran]-2,4'(3'H)-dione [ No CAS ]
5,7-dimethyl-6'-phenyl-5',6'-dihydrospiro[indoline-3,2'-pyran]-2,4'(3'H)-dione [ No CAS ]
5,7-dimethyl-6'-phenyl-5',6'-dihydrospiro[indoline-3,2'-pyran]-2,4'(3'H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-(pyridin-2-ylmethyl)pyrrolidine-2-carboxamide; ytterbium(III) triflate; In dichloromethane; at 20℃; for 288h;	General procedure: A mixture of Yb(OTf)3 (0.01 mmol) and ligand L6 (0.02 mmol) wasstirred at r.t. for 2 h in CH2Cl2 (2 mL). The appropriate enones 1 (1mmol) and isatins 2 (0.1 mmol) were then added. The resulting mixturewas stirred at r.t. After the reaction was completed as monitoredby TLC (eluent: hexane-EtOAc, 1:1), the reaction mixture was purifiedby column chromatography (silica gel, eluent: mixture ofhexane and EtOAc).

Reference： [1]Synthesis,2014,vol. 46,p. 1339 - 1347

34
[ 1013-88-3 ]
[ 39603-24-2 ]
[ 27532-96-3 ]
C₂₉H₃₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In 1,4-dioxane; at 20℃;	General procedure: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 586 - 589

35
[ 39603-24-2 ]
[ 107-97-1 ]
[ 1792-52-5 ]
C₂₃H₂₃N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,2,2-trifluoroethanol; for 0.666667h;Reflux;	General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4438 - 4444

36
[ 39603-24-2 ]
[ 1792-52-5 ]
[ 444-27-9 ]
C₂₄H₂₃N₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,2,2-trifluoroethanol; for 0.65h;Reflux;	General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4438 - 4444

37
[ 39603-24-2 ]
[ 107-97-1 ]
[ 54255-33-3 ]
C₂₃H₂₃N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,2,2-trifluoroethanol; for 0.666667h;Reflux;	General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4438 - 4444

38
[ 39603-24-2 ]
[ 54255-33-3 ]
[ 444-27-9 ]
C₂₄H₂₃N₃O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 2,2,2-trifluoroethanol; for 0.666667h;Reflux;	General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4438 - 4444

39
[ 39603-24-2 ]
[ 2835-77-0 ]
5,7-dimethyl-4'-phenyl-1'H-spiro[indoline-3,2'-quinazolin]-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With ammonium acetate; In ethanol; at 20℃; for 1.5h;Green chemistry;	General procedure: A mixture of 2-amino benzophenone (1 mmol), corresponding isatin or aldehyde (1 mmol) and ammonium acetate (2 mmol) in ethanol (5 mL) was stirred at room temperature. The progress of reaction was monitored by TLC. After completion of the reaction ice-cold water was added and stirred for a while. The solid product obtained was filtered and washed with water. This was further purified by crystallization from ethanol or by short column chromatographyon silica gel using ethyl acetate-petroleum ether as the eluent.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6373 - 6376

40
[ 606-23-5 ]
[ 39603-24-2 ]
[ 141-97-9 ]
ethyl 5',7'-dimethyl-1,1',2',5-tetrahydro-2-methyl-2',5-dioxospiro[4H-indeno[1,2-b]pyridine-4,3'-[3H]indole]-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With ammonium acetate; In ethanol; water; at 20℃; for 6h;Green chemistry;	General procedure: Isatin (1mmol), 1,3-indanedione (1mmol), ethyl acetoacetate (1mmol), and NH4OAc (1mmol) were placed in a 25-mL round-bottomed flask in ethanol:water (9:1) (5mL). The resulting mixture was stirred at room temperature for time mentioned in Table 2, until completion of the reaction as monitored by thin-layer chromatography (TLC). After completion of the reaction, the mixture was filtered and washed with a small quantity of ethanol to furnish pure spiro[4H-indeno-[1,2-b]pyridine-4,3'-[3H]indoles]. The structure of products was confirmed by IR, 1H and 13C NMR, GCMS, HRMS, and elemental analysis.

Reference： [1]Synthetic Communications,2015,vol. 45,p. 2498 - 2510

41
[ 39603-24-2 ]
[ 28144-70-9 ]
C₁₇H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With aminosulfonic acid; In ethanol; at 20℃; for 0.5h;Green chemistry;	General procedure: To a mixture of isatin(s)/acenaphthoquinone/cyclic ketone(s) (1 mmol) and anthranilamide (1mmol) in ethanol(96%, 2 mL), sulfamic acid (0.2 mmol) was added. Thereaction mixture was stirred at ambient temperature forthe time mentioned in table 2 until completion of reaction,as monitored by TLC. After the completion ofreaction, the precipitated products was just filtered. Theconfirmation of isolated products was done by spectraltechniques such as 1H, 13C NMR, IR and massspectrometry.

Reference： [1]Journal of Chemical Sciences,2016,vol. 128,p. 657 - 662

42
[ 39603-24-2 ]
[ 65359-62-8 ]
C₁₉H₂₃NO₄ [ No CAS ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 2482 - 2486

43
[ 39603-24-2 ]
[ 108-94-1 ]
[ 109-77-3 ]
3'-amino-5,7-dimethyl-2-oxo-6',7',8',8a’-tetrahydro-2'H-spiro[indoline-3,1'-naphthalene]-2',2',4'-tricarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; water; at 20℃; for 0.416667h;	General procedure: In a 25 cm3 round bottom flask, to a mixture of isatin(1 mmol), malononitrile (2 mmol), and cyclohexanone (1 mmol) in 10 cm3 30 % ethanol, DABCO (20 mol%)was added. The reaction mixture was stirred at room temperature for time mentioned in Table 2 until completionof reaction, monitored by TLC. After completion ofreaction, the mixture was cooled and filtered to furnish thedesired product in good yields.

Reference： [1]Monatshefte fur Chemie,2016,vol. 147,p. 1243 - 1249

44
[ 39603-24-2 ]
N-(6-((4-methylpiperidin-1-yl)methyl)benzo[d]thiazol-2-yl)hydrazinecarboxamide [ No CAS ]
(Z)-2-(5,7-dimethyl-2-oxoindolin-3-ylidene)-N-(6-((4-methylpiperidin-1-yl)methyl)benzo[d]thiazol-2-yl)hydrazinecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.5%	With acetic acid; In ethanol; for 6h;Reflux;	General procedure: A mixture of the compounds 11a-d (1 mmol) and substituted indolinone 15a-g (1.1 mmol) or appropriate aromatic aldehydes 12a-c (1.1 mmol) with catalyst amount of glacial acetic acid in ethanol (10 mL) was heated at reflux for 6 h and then cooled to room temperature and filtered. The obtained cake was washed with diethyl ether to get a white to light yellow solid. The crude product was purified by chromatography on silica gel using MeOH/CH2Cl2 to afford the desired compounds 16a-d and 17a-n.

Reference： [1]Medicinal Chemistry,2016,vol. 12,p. 489 - 498

45
[ 1072-98-6 ]
[ 39603-24-2 ]
[ 119072-55-8 ]
13-(tert-butylamino)-10-chloro-2,4-dimethyl-6-oxo-5,6-dihydropyrido[2',1':2,3]imidazo[1,5-c]quinazolin-12-ium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With perchloric acid; In butan-1-ol; for 8h;Reflux;	General procedure: To asolution of isatin 3 (1.0mmol), 2-aminopyridine 2 (1.35mmol)andisocyanide 4 (1.35mmol) in 4mL of n-butyl alcohol was added HClO4 (1.0mmol), and the reaction mixture was stirred under refluxfor 8 h. After cooling to room temperature, the precipitate was collected by filtration, rinsed with ethanol and dried to afford the target compound 1.
40%	With perchloric acid; In butan-1-ol; for 8h;Reflux;	Will be perchloric acid (70%, 1 mmol, 142 mg) was added 5-methoxyisatin (1 mmol, 177 mg), 2-amino-5-chloro-pyridine (1.35 mmol, 174 mg) And tert-butylisocyanide (1.35 mmol, 112 mg) in n-butanol (4 mL) The reaction was stirred at reflux for 8 hours. When the reaction solution was cooled to room temperature, Filtration and washing the filter cake with a small amount of ethanol gave the desired product in 39% yield.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1487 - 1492
[2]Patent: CN105017253,2017,B .Location in patent: Paragraph 0093-0096

46
[ 1072-98-6 ]
[ 39603-24-2 ]
[ 931-53-3 ]
10-chloro-13-(cyclohexylamino)-2,4-dimethyl-6-oxo-5,6-dihydropyrido[2',1':2,3]imidazo[1,5-c]quinazolin-12-ium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With perchloric acid; In butan-1-ol; for 8h;Reflux;	General procedure: To asolution of isatin 3 (1.0mmol), 2-aminopyridine 2 (1.35mmol)andisocyanide 4 (1.35mmol) in 4mL of n-butyl alcohol was added HClO4 (1.0mmol), and the reaction mixture was stirred under refluxfor 8 h. After cooling to room temperature, the precipitate was collected by filtration, rinsed with ethanol and dried to afford the target compound 1.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1487 - 1492

47
[ 39603-24-2 ]
[ 83-72-7 ]
[ 141-97-9 ]
5',7',8-trimethyl-5H-spiro[benzo[7,8]chromeno[2,3-c]pyrazole-7,3'-indoline]-2',5,6(9H)-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL×2) to afford the pure products as solid powder in good to excellent yields without further purification.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 1072 - 1075

48
[ 39603-24-2 ]
[ 35303-76-5 ]
4-(2-((5,7-dimethyl-2-oxoindolin-3-ylidene)amino)ethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid; In ethanol; for 2h;Reflux;	General procedure: To a stirred solution of the appropriate indolin-2,3-dione derivative1a-f (1 mmol) in absolute ethyl alcohol (10 mL), 4-(2-aminoethyl)benzenesulfonamide 2 (0.2 gm, 1 mmol) and catalyticamount of glacial acetic acid were added. After refluxing for 2 h, theformed precipitate was collected by filtration while hot, washedwith methanol, dried and crystallized from ethanol to furnishcompounds 3a-f with 62e75% yield.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 521 - 530
[2]Bioorganic Chemistry,2018,vol. 81,p. 425 - 432

49
[ 39603-24-2 ]
[ 107-97-1 ]
[ 55417-50-0 ]
ethyl 3'-cyano-1'-methyl-2-oxo-4′-(3,4-dichlorophenyl)spiro[5,7-dimethylindoline-3,2'-pyrrolidine]-3'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In 2,2,2-trifluoroethanol; at 150℃; for 0.133333h;Microwave irradiation; Green chemistry;	General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2873 - 2880

50
[ 39603-24-2 ]
[ 107-97-1 ]
[ 570419-39-5 ]
ethyl 3'-cyano-1'-methyl-2-oxo-4'-(2-chloro-6-fluorophenyl)spiro[5,7-dimethylindoline-3,2'-pyrrolidine]-3'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In 2,2,2-trifluoroethanol; at 150℃; for 0.166667h;Microwave irradiation; Green chemistry;	General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2873 - 2880

51
[ 39603-24-2 ]
[ 107-97-1 ]
[ 2286-35-3 ]
ethyl 3'-cyano-1'-methyl-2-oxo-4'-(4-chlorophenyl)phenylspiro[5,7-dimethylindoline-3,2'-pyrrolidine]-3'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In 2,2,2-trifluoroethanol; at 150℃; for 0.1h;Microwave irradiation; Green chemistry;	General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2873 - 2880

52
[ 39603-24-2 ]
[ 107-97-1 ]
[ 2286-29-5 ]
ethyl 3'-cyano-1'-methyl-2-oxo-4'-(4-methoxyphenyl)spiro[5,7-dimethylindoline-3,2'-pyrrolidine]-3'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In 2,2,2-trifluoroethanol; at 150℃; for 0.133333h;Microwave irradiation; Green chemistry;	General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2873 - 2880

53
[ 61-54-1 ]
[ 39603-24-2 ]
5,7-dimethyl-2',3',4',9'-tetrahydrospiro[indoline-3,1'-pyrido[3,4-b]indol]-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sulfonated beta-cyclodextrin; In water; at 80℃;Green chemistry;	General procedure: Sulfonated-beta-cyclodextrin (beta-CD-SO3H) (76 mg, 0.06 mmol) was dissolved in water (5 mL) at RT by stirring to get the clear solution in 50 mL round bottom ask. Further, isatin 2 (0.31 mmol) and tryptamine 1a/isotryptamine 1b (0.31 mmol) were added to the solution under constant stirring and mixture was heated at 80 C for 8-12 h. The progress of the reaction was monitored by TLC. After completion of reaction, it was cooled to room temperature, water was added to it. The aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product obtained was puried by column chromatography using chloroform/methanol (99:1) as an eluent furnishing the product. The spectral and analytical data of all the reported products is consistent with the previous (6c,d,f) reports.

Reference： [1]Tetrahedron,2017,vol. 73,p. 4348 - 4354

54
[ 39603-24-2 ]
[ 23911-56-0 ]
6,8-dimethyl-2-(3-methyl-1-benzofuran-2-yl)quinoline-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With ethanol; potassium hydroxide; at 80℃; for 16h;	j0309j A. 6,8-Dimethyl-2-(3-methyl-1-benzofuran-2-yl)quinoline-4-carboxylic acid. To a100 ml. round-bottom flask was placed a solution of 1-(3-methyl-1-benzofuran-2-yl)ethan-1-one (1 g,5.74 mmol) in EtOH (20 mL) then 5,7-dimethyl-2,3-d1H ydro-1H -indole-2,3-dione(800 mg,4.57 mmol) and KOH (800 mg) were added. The resulting solution was heated to80C and stirred for 16 h. The reaction was cooled to rt and concentrated under reducedpressure. The residue was dissolved in 100 mL of H20,washed with MTBE (3x50 mL),and the pH of the solution was adjusted to 2-3 with 2N HC1. The resulting precipitate was isolated by filtration and washed with MeOH (3x50 mL) affording 485 mg (32%) of the title compound as a yellow solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C2,H,8NO3: 332.1 (M+H); Found: 332.0. 1H NMR (300 MHz,DMSO-d6): oe 13.95 (s,1H ),8.43 (s,1H ),8.33 (s,1H ),7.80-7.77 (d,J= 7.5 Hz,1H ),7.73-7.70 (d,J= 8.1H z,1H ),7.61 (s,1H ),7.47-7.42 (t,J= 7.5 Hz,1H ),7.38-7.33 (t,J= 7.5 Hz,1H ),2.85 (s,3H),2.73 (s,3H),2.52 (s,3H). HPLC purity(254 nm): 99.5%.

Reference： [1]Patent: WO2017/62581,2017,A1 .Location in patent: Paragraph 0309

55
[ 39603-24-2 ]
[ 79-08-3 ]
[ 621-01-2 ]
5-(5-methyl-2-oxoindolin-3-ylidene)-3-(p-tolyl)-2-(p-tolylimino)thiazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: A mixture of isatins 1a-g (1 mmoL) with an equimolar amount of N,N'-diphenyl/(p-tolyl)thiourea2a,b (1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in the presenceof sodium acetate (0.16 gm, 2 mmoL), was heated under reflux for 3 h. The formed solid was filteredoff while hot, washed with hot ethanol, dried and recrystallized from DMF to furnish the targethybrids 4a-n.

Reference： [1]Molecules,2018,vol. 23

56
[ 39603-24-2 ]
[ 79-08-3 ]
[ 134469-07-1 ]
2-(5,7-dimethyl-2-oxoindolin-3-ylidene)benzo[4,5]imidazo[2,1-b]thiazol-3(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium acetate; acetic acid; for 2h;Reflux;	General procedure: A mixture of isatins 1c, e-g (1 mmoL) with an equimolar amount of 2-mercaptobenzimidazole6 (0.15 gm, 1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in thepresence of sodium acetate (0.16 g, 2 mmoL), was heated under reflux for 2 h. The obtained solid wasfiltered off while hot, washed with hot ethanol, dried and recrystallized from DMF to afford the targethybrids 7a-d.

Reference： [1]Molecules,2018,vol. 23

57
[ 39603-24-2 ]
[ 79-08-3 ]
[ 102-08-9 ]
5-(5,7-dimethyl-2-oxoindolin-3-ylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: A mixture of isatins 1a-g (1 mmoL) with an equimolar amount of N,N'-diphenyl/(p-tolyl)thiourea2a,b (1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in the presenceof sodium acetate (0.16 gm, 2 mmoL), was heated under reflux for 3 h. The formed solid was filteredoff while hot, washed with hot ethanol, dried and recrystallized from DMF to furnish the targethybrids 4a-n.

Reference： [1]Molecules,2018,vol. 23

58
[ 39603-24-2 ]
[ 100-52-7 ]
3-hydroxy-6,8-dimethyl-4-phenylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3639 - 3642

59
[ 39603-24-2 ]
[ 104-88-1 ]
4-(4-chlorophenyl)-3-hydroxy-6,8-dimethylquinolin-2(1H)-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3639 - 3642

60
[ 39603-24-2 ]
[ 35264-29-0 ]
4-[2-(5,7-dimethyl-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With acetic acid; for 6h;Reflux;	General procedure: To a hot solution of 4-(hydrazinecarbonyl)benzenesulfonamide 3 (0.25g, 1.16mmol) in glacial acetic acid (15mL), the appropriate isatin derivative 4a-h, 8a-g or 9a-c (1.2mmol) was added. This mixture was heated under reflux for 6h. The formed precipitate was filtered off while hot and washed with ethanol and petroleum ether then recrystallized from DMF/ethanol to obtain the target compounds 5a-h, 10a-g and 11a-c.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 28 - 36

61
[ 39603-24-2 ]
benzyl halide [ No CAS ]
[ 1017609-55-0 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4759 - 4763

62
[ 1076-38-6 ]
[ 39603-24-2 ]
[ 40400-15-5 ]
5',7'-dimethyl-6H,12H-spiro[chromeno[3',4':5,6]pyrano[2,3-b]indole-7,3'-indoline]-2',6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,7-bis(((pyridin-2-ylmethyl)amino)methyl)-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diol; potassium hydroxide; palladium dichloride; In dimethyl sulfoxide; at 110℃;	isatin(1.0 mmol) was added to a 50 mL dry round bottom flask in turn.O-iodophenylacetonitrile (1.0 mmol), 4-hydroxycoumarin (1.0 mmol),Catalyst 3e (5 mol%), palladium dichloride (5 mol%),KOH (20 mol%), DMSO 3 mL, mix well, stir at 110 C,After the reaction was completed (TLC tracking), an appropriate amount of water was added and extracted with ethyl acetate.The organic phases are combined, and the excess solvent in the system is distilled off under reduced pressure.The crude product was separated by column chromatography (V petroleum ether: V ethyl acetate = 1:1 gradient elution) to give the title compound 12b in a yield of 85%.

Reference： [1]Patent: CN109305970,2019,A .Location in patent: Paragraph 0197-0207

63
[ 39603-24-2 ]
[ 14243-64-2 ]
C₂₈H₂₃AuNO₂P [ No CAS ]

Reference： [1]Dalton Transactions,2019,vol. 48,p. 3098 - 3108

64
[ 39603-24-2 ]
[ 18024-34-5 ]
C₄₆H₄₀Au₂N₂O₄P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With caesium carbonate In dichloromethane at 20℃; for 24h;

Reference： [1]Fernández-Moreira, Vanesa; Val-Campillo, Cynthia; Ospino, Isaura; Herrera, Raquel P.; Marzo, Isabel; Laguna, Antonio; Gimeno, M. Concepción [Dalton Transactions, 2019, vol. 48, # 9, p. 3098 - 3108]

65
[ 39603-24-2 ]
[ 53-43-0 ]
C₂₉H₃₅NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium fluoride on basic alumina; In ethanol; for 6h;Reflux;	General procedure: To a solution of DHEA (0.5 mmol, 1.0 eq) and isatin derivative(0.75 mmol, 1.5 eq) in EtOH (10 mL) was added Al2O3/KF (0.5 mmol,1.0 eq), the resulting mixture was stirred at reflux temperature for 6 h.Upon completion of the reaction indicated by the TLC, the mixture wasfiltered and the solid was washed with dichloromethane (DCM) forseveral times. The filtrate was then evaporated under vacuum, followedby addition of DCM and H2O. The mixture was then acidified with 4MHCl (pH=1-2). The aqueous layer was washed with DCM for severaltimes. The combined organic layers were then dried over Na2SO4 andevaporated under vacuum to the crude product, which was then subjectedto column chromatography, affording the corresponding product.

Reference： [1]Steroids,2019,vol. 151

66
[ 39603-24-2 ]
3-ethylisoxazol-5(4H)-one [ No CAS ]
[ 31230-17-8 ]
3'-ethyl-5,5',7-trimethyl-6',8'-dihydrospiro[indoline-3,4'-isoxazolo[5,4-b]pyrazolo[4,3-e]pyridin]-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With Amberlyst-15; In methanol; at 80℃; for 5h;	General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

Reference： [1]Tetrahedron Letters,2019,vol. 60

67
[ 39603-24-2 ]
[ 6642-31-5 ]
[ 1076-59-1 ]
1',3',6,8-tetramethyl-3-phenyl-9H-spiro[isoxazolo[5,4-b]quinoline-4,5'-pyrrolo[2,3-d]pyrimidine]-2',4',6'(1'H,3'H,7'H)-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With Amberlyst-15; In methanol; at 80℃; for 5h;	General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

Reference： [1]Tetrahedron Letters,2019,vol. 60

68
[ 39603-24-2 ]
[ 60-80-0 ]
4,4'-(5,7-dimethyl-2-oxoindoline-3,3-diyl)bis(1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In water; at 120℃; for 48h;Green chemistry;	General procedure: The mixture of isatin 1 (29.4 mg, 0.2 mmol), antipyrine 2a (84.7 mg, 0.45 mmol) in 1mL H2O were stirred at 120 . Once the reaction completed (indicated by colorchange from red to white), the mixture was then cooled down to the room temperature.The insoluable solid mixture was filtered, washed by water and dried under vacuum to afford the desired product 4a in high pure form.

Reference： [1]Tetrahedron,2020,vol. 76

69
[ 39603-24-2 ]
[ 141-97-9 ]
ethyl (R)-4-(3-hydroxy-5,7-dimethyl-2-oxoindolin-3-yl)-3-oxobutanoate [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 6 - 10

70
[ 39603-24-2 ]
[ 147-85-3 ]
alkyl 2‐[hydroxy(phenyl)methyl]prop‐2‐enoate [ No CAS ]
2,4-dimethyl-14-phenyl-7a,8,9,10-tetrahydro-7H-6a,11a-(methanooxymethano)pyrrolizino[2,3-c]quinoline-6,12(5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 0.166667h;Sealed tube; Microwave irradiation;	General procedure: All microwave irradiation experiments were carried out in an Anton Paar Monowave 200 apparatus. Isatin 1 (1.0 equiv.) L-proline, 2 (1.0 equiv.), Baylis-Hillman adduct 3 (1.0 equiv.) and CuI (20 mol%) were suspended in DMF (2 mL) and placed in a 10 mL reaction vial, which was sealed with a septum and irradiated with microwave 200 for 10 min at 80 C. The reaction mixture was allowed to cool to r.t. and then diluted with CH2Cl2 (10 mL) and filtered. The organic layer was separated and the solvent was evaporated under reduced pressure and the resulting residue was purified by column chromatography to afford the pure polycyclic pyrrolidine- and piperidinoquinolinone derivatives.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 973 - 979

71
[ 39603-24-2 ]
[ 5448-47-5 ]
N'-(5,7-dimethyl-2-oxoindolin-3-ylidene)-2-(1H-indol-3-yl)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With acetic acid; In ethanol; for 2h;Reflux;	General procedure: To a hot stirred solution of key intermediate 1H-indole-2-carbohydrazide 5 (0.18 gm, 1 mmoL) inabsolute ethyl alcohol (7 mL) and glacial acetic acid (catalytic amount), the appropriate N-unsubstituted1H-indole-2,3-dione 6a-f, N-substituted 1H-indole-2,3-dione 8a-h, or 1-tetralone 10 (1 mmoL) wasadded. The resulting mixture was refluxed for 2 hours, and then the formed solid was filtered owhile hot, washed with cold isopropyl alcohol, dried and recrystallized from DMF to aord targetbis-indoles (7a-f and 9a-h), and 11, respectively.

Reference： [1]Marine Drugs,2020,vol. 18

72
[ 39603-24-2 ]
[ 5055-39-0 ]
N'-(5,7-dimethyl-2-oxoindolin-3-ylidene)-1H-indole-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid; for 4h;Reflux;	General procedure: A solution of indole-2-carbohydrazide 4 (210 mg, 1.2 mmol) in glacial acetic acid (15 mL) was treated with the appropriate isatin derivative 5a-i and 8a-f (1.2 mmol), or ketones 10a and 10b (1.2 mmol). The resulting reaction mixture was refluxed for four hours then cooled to r.t. The obtained precipitate was collected by filtration and dried to get a powder that was recrystallized from glacial acetic acid to furnish the titled conjugates 6a-i, 9a-f, and 11a,b.

Reference： [1]Molecules,2020,vol. 25

73
[ 39603-24-2 ]
[ 131-58-8 ]
3-(2-benzoylbenzyl)-3-hydroxy-5, 7-dimethylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With air In toluene at 25℃; UV-irradiation; Green chemistry;	2.3. General procedure for the preparation of 3-alkyl-3-hydroxyindolin-2-ones General procedure: A quartz tube equipped with a stirring bar was charged with isatin derivative (0.20 mmol, 1.0 equiv.), benzophenone compound (0.30 mmol, 1.5 equiv.), and toluene (2 mL). The mixture was stirred at room temperature under irradiation of a 15 W black LEDs (Philips) in the air atmosphere. After completion of the reaction (detected by TLC), the toluene was removed from the reaction mixture. The residue was purified by flash chromatography on silica gel with petroleum ether/ethyl acetate (5:1 to 2:1) as the eluent to give desired product.
65%	In toluene at 20℃; for 36h; UV-irradiation;	13 Example 13 Dissolve 0.2mmol of compound III-13 (5,7-dimethylindoline-2,3-dione) and 0.3mmol of compound II-13 (phenyl(o-tolyl)methanone) in 2ml of organic solvent (toluene), irradiate with an ultraviolet lamp with a power of 15W, react at room temperature for 36h, and purify by chromatography after removing the organic solvent (using a volume ratio of 2:1 petroleum ether and ethyl acetate mixed solvent as eluent, R f value=0.2) to obtain a white solid compound I-13 (3-(2-benzoylbenzyl)-3-hydroxy-5,7-dimethylindolin-2-one) (Mp is 191.6-193.3 ) 48.3mg, the yield is 65%,

Reference： [1]Wang, Zhi-Lv; Tang, Li; Zeng, Wei-Mei; He, Yan-Hong; Guan, Zhi [Tetrahedron Letters, 2022, vol. 95]
[2]Current Patent Assignee: SOUTHWEST UNIVERSITY - CN113801054, 2021, A Location in patent: Paragraph 0100-0105

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P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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. 39603-24-2 ] {[proInfo.proName]}

Quality Control of [ 39603-24-2 ]

Related Doc. of [ 39603-24-2 ]

Product Details of [ 39603-24-2 ]

Calculated chemistry of [ 39603-24-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 39603-24-2 ]

Application In Synthesis of [ 39603-24-2 ]

[ 39603-24-2 ] Synthesis Path-Upstream 1~9

[ 39603-24-2 ] Synthesis Path-Downstream 1~73

Related Functional Groups of [ 39603-24-2 ]

Amides

Ketones

Related Parent Nucleus of [ 39603-24-2 ]

Indolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 39603-24-2 ]

Related Parent Nucleus of
[ 39603-24-2 ]