Type: Article

A one-pot, three-component synthesis of spiro[indoline-isoxazolo[40,30:5,6] pyrido [2,3-d]pyrimidine]triones in water

Journal: Tetrahedron (00404020)Year: 2012/10/07Volume: 68Issue: 40Pages: 8472 - 8479

a :University of Isfahan - IRAN(IR) - Isfahan

DOI:10.1016/j.tet.2012.07.073Language: English

Abstract

A one-pot, three-component condensation reaction of an isatin, isoxazole, and barbituric acid in water to give spirooxindoles in high yields, at 70°C temperature, using a catalytic amount of p-toluene sulfonic acid, is described. © 2012 Elsevier Ltd. All rights reserved.

Author Keywords

1,4-DihydropyridinesIsatinSpirooxindole1,1' (propane 1,3 diyl)bis isatin1,1' (propane 1.3 diyl)bis isatin1,3' dimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (6'h,8'h,9'h)trione3' methyl 5 nitrospiro[indolin 3,4' isoxazolo[ 4'.3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3' methyl 7' thiohydroxyspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5' (1h,6'h,9'h)dione3' methyl spiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3',5,7 trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3,6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione4 toluene sulfonic acid5 bromo 3' methylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5 bromo 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 chloro 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 chloro 6',8' diethyl 3' methyl 7' thioxospiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5' (1h,9'h)dione5 iodo 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 nitro 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5' chloro 3 methylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5,3' dimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5,3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trionebarbituric acidindole derivativeisatinisatin derivativeisoxazolepyrido[2,3 d]pyrimidine derivativetoluenesulfonic acid derivativeunclassified drugwater

Other Keywords

1,1' (propane 1,3 diyl)bis isatin1,1' (propane 1.3 diyl)bis isatin1,3' dimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (6'h,8'h,9'h)trione3' methyl 5 nitrospiro[indolin 3,4' isoxazolo[ 4'.3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3' methyl 7' thiohydroxyspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5' (1h,6'h,9'h)dione3' methyl spiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3',5,7 trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione3,6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione4 toluene sulfonic acid5 bromo 3' methylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5 bromo 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 chloro 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 chloro 6',8' diethyl 3' methyl 7' thioxospiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5' (1h,9'h)dione5 iodo 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5 nitro 3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trione5' chloro 3 methylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5,3' dimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,6'h,8'h,9'h)trione5,3',6',8' trimethylspiro[indolin 3,4' isoxazolo[ 4',3':5,6 ]pyrido[2,3 d]pyrimidine] 2,5',7' (1h,9'h)trionebarbituric acidindole derivativeisatinisatin derivativeisoxazolepyrido[2,3 d]pyrimidine derivativetoluenesulfonic acid derivativeunclassified drugwaterarticlecatalysischemical reactioncontrolled studydrug synthesismulticomponent reactionone pot synthesispolymerizationpriority journalroom temperature