41042-12-0|1-Propyl-1H-indole-2,3-dione| Ambeed

Structure of 41042-12-0

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Quality Control of [ 41042-12-0 ] Purity: 95% SDS Specification

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Product Details of [ 41042-12-0 ]

CAS No. :	41042-12-0
Formula :	C₁₁H₁₁NO₂
M.W :	189.21
SMILES Code :	O=C1N(CCC)C2=C(C=CC=C2)C1=O
MDL No. :	MFCD00224226
InChI Key :	SSUNBCWMOHUMAX-UHFFFAOYSA-N
Pubchem ID :	1645090

Safety of [ 41042-12-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Computational Chemistry of [ 41042-12-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.27
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	56.67
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.38 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.25
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.08
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.12
Solubility	1.42 mg/ml ; 0.00751 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.86
Solubility	2.6 mg/ml ; 0.0138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.26
Solubility	0.104 mg/ml ; 0.000548 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.41 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.76

Application In Synthesis of [ 41042-12-0 ]

* 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.

Downstream synthetic route of [ 41042-12-0 ]

[ 41042-12-0 ] Synthesis Path-Downstream 1~35

1
[ 188290-36-0 ]
[ 41042-12-0 ]
C₃₄H₃₀N₂O₂S₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 11512 - 11515.

2
[ 41042-12-0 ]
[ 613-94-5 ]
[ 1048973-61-0 ]

References: [1]New Journal of Chemistry,2019,vol. 43,p. 8122 - 8131.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 4932 - 4947.

3
[ 91-56-5 ]
[ 106-94-5 ]
[ 41042-12-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; In N,N-dimethyl-formamide; for 0.05h;Microwave irradiation;	General procedure: To a solution of isatin 3a (0.03mol) in DMF (7mL), the corresponding alkyl halides (0.03mol) and K2CO3 (0.042mol, 6.20g) were added. Reaction mixture was microwave irradiated for an appropriate time and then cooled to room temperature and mixed thoroughly with ice-water. The product recrystallized from the suitable solvent. Reaction time, yield, melting point and recrystallization solvents for these N-alkylisatins are following: N-methylisatin (3m), 2min, 84%, 130-131C (96% ethanol), ref [39]: 130-133C; N-ethylisatin (3n), 3min, 71%, 86-87C (96% ethanol), ref [39]: 88-89C; N-propylisatin (3o), 3min, 75%, 196-197C (96% ethanol), ref [39]: 198C; N-butylisatin (3p), 4min, 63%, 34-36C (diethyl ether), ref [6]: 36C; N-allylisatin (3r), 2min, 72%, 90-91C (96% ethanol), ref [39]: 88-89C; N-benzylisatin (3s), 3min, 88%, 129-130C (96% ethanol), ref [39]: 131-132C. Compounds 3q and 3t were prepared similarly and used for synthesis of corresponding thiosemicarbazones.
70%	With potassium carbonate; In N,N-dimethyl-formamide; for 4h;Reflux;	General procedure: Isatins 6a,c (3.4 mmol) were stirred in DMF (15 mL) with (3.7 mmol) of the appropriate alkyl/benzyl halide derivatives 8a-g in the presence of anhydrous potassium carbonate (1.24 g, 9mmol) at reflux temperature for 4 hrs. Then, the mixture was poured onto ice/water, and theformed solid was collected by filtration, washed with water, dried and recrystallized from ethanolto furnish compounds 9a-i. (Yield 68-86%)
68%	With potassium carbonate; In N,N-dimethyl-formamide; at 60 - 70℃; for 3h;	General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60-70C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95%) togive N-alkylated isatins as red crystalls in 37-92% yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2-4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4·H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47-96% yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60% dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of -15 C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3'-indolin]-2'-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3'-indolin]-2'-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7-11).

60%	With potassium carbonate; sodium iodide; In acetonitrile; at 20℃; for 120h;Inert atmosphere; Molecular sieve;	To an oven dried flask equipped with a stir bar cooled under argon was added isatin (2.0 grams, 13.6 mmol, 1.0 equiv., purchased from Fisher Scientific), potassium carbonate (9.67 grams, 5.0 equiv.), and sodium iodide (0.209 grams, 1.4 mmol, 0.1 equiv.). The mixture was taken up in acetonitrile (60.0 μL, stored over 4 angstrom molecular sieves). While stirring at room temperature the appropriate propyl bromide (1.4 mL, 15 mmol, 1.1 equiv.) was added. After five days of stirring at room temperature, the solution was filtered, concentrated, and taken up in dichloromethane. The solution was next filtered again, and concentrated. Purification was done on a silica gel column using hexanes/ethyl acetate, to afford a red solid, 1.5 grams (60% yield). 1H-NMR δ 7.59 (m, 2H), 7.12 (dd, 1H), 6.90 (d, 1H), 3.70 (t, 2H), 1.75 (m, 2H), 1.00 (t, 3H).
		General procedure: The isatin/5-chloroisatin1(1 equiv.) and solid K2CO3 (1.2 equiv.) were taken ina 100 ml round bottom flask containing DMF (30 ml) as the solvent and thereaction was stirred for half-an-hour.The appropriate alkyl/benzyl bromide 2(1.2 equiv.) was added to the reaction mixture and stirred continuously for10-12 h until the starting material was consumed (monitored by TLC). Thereaction mixture was diluted with water (50 mL) and extracted with EtOAc (2 ×50 mL). The organic layer was washed with brine (2 × 50 mL), dried over anhydrousNa2SO4 and filtered. The filtrate was evaporated and thecrude product was purified by using silica gel column chromatography (EtOAc:hexane = 3:7; Rf 0.7), as the red solid products (3 and 4) in 70-80% yields. The structures were established on the basisof their spectroscopic data and these were identical in all respects to thosereported earlier.[1,2]
	With sodium hydride; In N,N-dimethyl-formamide; at 20℃;	General procedure: Isatin derivatives (S1) were synthesized by treating isatins with NaH and then reacting with methyl iodide or benzyl bromide or allyl bromide, respectively, in dry DMF at room temperature.
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; for 3h;Reflux;	General procedure: To a stirred mixture of isatins 3a-c (3.4 mmol), potassium carbonate(0.94 g, 6.8 mmol) and catalytic amount of potassium iodidein dry DMF (10 mL), the appropriate alkyl halide 5a-d (3.7 mmol) or benzyl bromide 5e (0.63 g, 3.7 mmol) was added, and the mixture was heated under reflux for 3 h. Then, the reaction mixture was poured into ice-water, the obtained solid was collected, washed several times with water, and recrystallized from ethyl alcohol to afford the N-substituted isatin derivatives 6a-o [27].

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4932 - 4947.
[2]Green Chemistry,2015,vol. 17,p. 4194 - 4197.
[3]European Journal of Medicinal Chemistry,2016,vol. 123,p. 532 - 543.
[4]Bioorganic Chemistry,2021,vol. 110.
[5]Tetrahedron Letters,2018,vol. 59,p. 3409 - 3412.
[6]Patent: US2014/275075,2014,A1 .Location in patent: Paragraph 0158; 0159; 0160.
[7]Asian Journal of Chemistry,2015,vol. 27,p. 2911 - 2916.
[8]Journal of Enzyme Inhibition and Medicinal Chemistry,2018,vol. 33,p. 686 - 700.
[9]European Journal of Medicinal Chemistry,2018,vol. 157,p. 28 - 36.
[10]European Journal of Medicinal Chemistry,2019,vol. 162,p. 448 - 454.
[11]Tetrahedron,2019,vol. 75,p. 1689 - 1696.
[12]New Journal of Chemistry,2019,vol. 43,p. 8122 - 8131.
[13]European Journal of Medicinal Chemistry,2019,vol. 184.
[14]Molecules,2020,vol. 25.
[15]Journal of Enzyme Inhibition and Medicinal Chemistry,2021,vol. 36,p. 319 - 328.
[16]Journal of Enzyme Inhibition and Medicinal Chemistry,2021,vol. 36,p. 384 - 393.
[17]Journal of Enzyme Inhibition and Medicinal Chemistry,2021,vol. 36,p. 1424 - 1435.
[18]Organic and Biomolecular Chemistry,2022,vol. 20,p. 808 - 816.

4
[ 41042-12-0 ]
[ 536-74-3 ]
[ 1172590-88-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1,4-diaza-bicyclo[2.2.2]octane; copper(II) tungstate; In water; at 60℃;Green chemistry;	General procedure: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

References: [1]Catalysis Communications,2020,vol. 135.
[2]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 217 - 220.
[3]European Journal of Organic Chemistry,2021,vol. 2021,p. 5348 - 5358.

5
[ 41042-12-0 ]
[ 1258856-78-8 ]

References: [1]Russian Journal of Organic Chemistry,2014,vol. 50,p. 822 - 828.
Zh. Org. Khim.,2014,vol. 50,p. 839 - 845,7.
[2]Synthesis,2010,p. 3268 - 3270.

6
[ 108-48-5 ]
[ 41042-12-0 ]
[ 1356219-71-0 ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.
[2]Organic Letters,2012,vol. 14,p. 676 - 679.
[3]Cuihua Xuebao/Chinese Journal of Catalysis,2012,vol. 33,p. 1636 - 1641.

7
[ 1239867-49-2 ]
[ 41042-12-0 ]

References: [1]RSC Advances,2013,vol. 3,p. 5824 - 5827.

8
[ 756876-36-5 ]
[ 41042-12-0 ]

References: [1]Chemical Communications,2013,vol. 49,p. 8540 - 8542.

9
[ 109-06-8 ]
[ 41042-12-0 ]
C₁₇H₁₈N₂O₂ [ No CAS ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.

10
[ 108-89-4 ]
[ 41042-12-0 ]
C₁₇H₁₈N₂O₂ [ No CAS ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.

11
[ 95-21-6 ]
[ 41042-12-0 ]
C₁₉H₁₈N₂O₃ [ No CAS ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.

12
[ 120-75-2 ]
[ 41042-12-0 ]
C₁₉H₁₈N₂O₂S [ No CAS ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.

13
[ 615-15-6 ]
[ 41042-12-0 ]
C₁₉H₁₉N₃O₂ [ No CAS ]

References: [1]RSC Advances,2013,vol. 3,p. 20281 - 20286.

14
[ 41042-12-0 ]
[ 536-74-3 ]
[ 609-36-9 ]
3-(2-(phenylethynyl)pyrrolidin-1-yl)-1-propylindolin-2-one [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 9412 - 9415.

15
[ 41042-12-0 ]
[ 120329-58-0 ]
[ 1642594-11-3 ]

Yield	Reaction Conditions	Operation in experiment
48%	With hexaethylphosphoric triamide; In 1,2-dichloro-benzene; at -10℃; for 8h;	General procedure: tris(diethylamino)phosphine (0.1 g,0.4 mmol) was added dropwise to a mixture of the corresponding isatins A 2-9 (0.14 mmol) and C60 (0.1 g, 0.14 mmol) in anhydrous o-dichlorobenzene (40 mL) at -10 . The mixture was stirred for 8 h at -10 and then the temperature was allowed to rise to room temperature. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using a mixture of toluene and petroleum ether 4:5 as eluent. After elution of the recovered C60, the fraction containing the desired compound was collected and dried in vacuo at 30-40 C for 6 h.

References: [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1121 - 1128.

16
[ 41042-12-0 ]
3-hydroxy-1-propylindolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; water; In tetrahydrofuran; at 0 - 20℃;	To a dry clean round bottom equipped with a stir bar was added <strong>[41042-12-0]1-propylindoline-2,3-dione</strong> (1 gram, 5.3 mmol) 12 mL of THF and 6 mL of water. While stirring at 0 C. solid sodium borohydride (0.300 grams, 7.93 mmol) was added. The stirring solution was slowly warmed up to room temperature. After all the color had disappeared the reaction was quenched with 1.0 M HCl and diluted with dichloromethane. The organic layer was removed. The aqueous layer was washed two more time with dichloromethane. The combined organic solution was dried with sodium sulfate, filtered and concentrated. It was then used in the subsequent step without further purification.
	With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0℃;	General procedure: 3-OBoc-oxindoles 3a and 3e-g were synthesized by following our earlier reportedproceudure.1 In a 100ml round bottom flask was charged with 1g of N-protected isatin, 1equivalent of CeCl3.7H2O and the mixture was dissolved by methanol (2mL/mmol) then0.5equivalent of NaBH4 was added portion wise at 0 C. After addition of NaBH4 the reactionmixture was quenched imidiately by excess of ice and taken extract with ethylacetate twice. Theorganic fractions was combined and dried over anhydrous Na2SO4 and evaporated through rotary vacuum.

References: [1]Patent: US2014/275075,2014,A1 .Location in patent: Paragraph 0228; 0229.
[2]Organic Letters,2015,vol. 17,p. 1066 - 1069.

17
[ 41042-12-0 ]
[ 504-02-9 ]
[ 106-47-8 ]
[ 762-42-5 ]
C₂₉H₂₇ClN₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With zinc ferrite; In water; at 20℃; for 2h;Green chemistry;	General procedure: A mixture of arylamines(1.0 mmol), acetylenedicarboxylates (1.0 mmol), isatins (1.0 mmol), and cyclic 1,3-diketones (1.0 mmol) was taken in a 100 ml round bottom flask. Then 10 ml water and 20 mol % of the ZnFe2O4 nanopowder were added to the flask. The resultant mixture was stirred for 2 h at room temperature. After completion of the reaction (when the starting materials were completely disappeared as per thin layer chromatography projection), the reaction mixture was ultrasonicated by ethyl acetate (10 ml) for 10 min. The separated organic phase was concentrated to get the crude product which was purified by silica gel column chromatography (ethyl acetate/hexanes) to afford the spiro-compounds (5a-e0 ). The solid catalyst was collected from water layer by simple filtration with sintered funnel. The recovered catalyst was washed several times with water, ethyl acetate and finally by acetone, dried in a desiccator and used for another run.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 1654 - 1660.

18
[ 41042-12-0 ]
[ 126-81-8 ]
[ 104-94-9 ]
[ 762-42-5 ]
C₃₂H₃₄N₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With zinc ferrite; In water; at 20℃; for 2h;Green chemistry;	General procedure: A mixture of arylamines(1.0 mmol), acetylenedicarboxylates (1.0 mmol), isatins (1.0 mmol), and cyclic 1,3-diketones (1.0 mmol) was taken in a 100 ml round bottom flask. Then 10 ml water and 20 mol % of the ZnFe2O4 nanopowder were added to the flask. The resultant mixture was stirred for 2 h at room temperature. After completion of the reaction (when the starting materials were completely disappeared as per thin layer chromatography projection), the reaction mixture was ultrasonicated by ethyl acetate (10 ml) for 10 min. The separated organic phase was concentrated to get the crude product which was purified by silica gel column chromatography (ethyl acetate/hexanes) to afford the spiro-compounds (5a-e0 ). The solid catalyst was collected from water layer by simple filtration with sintered funnel. The recovered catalyst was washed several times with water, ethyl acetate and finally by acetone, dried in a desiccator and used for another run.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 1654 - 1660.

19
[ 41042-12-0 ]
[ 99-61-6 ]
C₁₈H₁₆N₄O₂ [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 28163 - 28170.

20
[ 606-23-5 ]
[ 41042-12-0 ]
[ 36646-77-2 ]
C₃₃H₂₈N₂O₄ [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 31866 - 31877.

21
[ 606-23-5 ]
[ 41042-12-0 ]
[ 41609-04-5 ]
C₃₃H₂₈N₂O₃ [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 31866 - 31877.

22
[ 606-23-5 ]
[ 41042-12-0 ]
3-[(4-bromophenyl)amino]cyclohex-2-en-1-one [ No CAS ]
C₃₂H₂₅BrN₂O₃ [ No CAS ]

References: [1]RSC Advances,2015,vol. 5,p. 31866 - 31877.

23
[ 41042-12-0 ]
2,4-dichlorophenylacetylhydrazide [ No CAS ]
(E)-2-(2,4-dichlorophenyl)-N'-(2-oxo-1-propylindolin-3-ylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol;Reflux;	General procedure: Isatin based Schiff bases (1-20) were synthesized in three steps,first an esterification carried out by reacting different carboxylicacid with methanol in sulphuric acid (2-3 ml) under reflux conditionfor 12-16 h. The completion of reaction was monitored byTLC. After completion of reaction, reaction mixture was extractedwith hexane to obtained pure esters. Then esters were refluxedwith hydrazine hydrate in methanol with few drops of glacial aceticacid for 3 h. After completion of reaction, reaction mixture waswashed with chloroform to obtained different hydrazides. Thesehydrazides (1mmole) each were than treated with different Isatin(1mmole) in methanol having catalytic amount of glacial acetic acidfor 2-4 h. Reaction completion was monitored through periodicTLC. After completion of reaction, reaction mixture was washedwith n-hexane to obtain our desired products (1-20). The structureof all compounds was established through EI-MS and 1H NMR.