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Three-Component Reaction for Construction of Spiro[indoline- 3,7'-thiazolo[3,2-a]pyridines] and Spiro[benzo[4,5]- thiazolo[3,2-a]pyridine-3,3'-indolines]

Three-Component Reaction for Construction of Spiro[indoline- 3,7'-thiazolo[3,2-a]pyridines] and Spiro[benzo[4,5]- thiazolo[3,2-a]pyridine-3,3'-indolines]
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摘要 The three-component reaction of thiazole (benzothiazole), dialkyl but-2-ynedioate, and isatinylidene malononi- triles in toluene at 110-120 ℃ in a sealed tube afforded a mixture of cis/trans-isomers of functionalized di- astereoisomeric spiro[indoline-3,7'-thiazolo[3,2-a]pyridines] and spiro[benzo[4,5]thiazolo[3,2-a]pyridine-3,3'-in- dolines] in good yields. Both cis-isomers and trans-isomers were successfully separated out and fully characterized with spectroscopy and single crystal determination. Under similar conditions, the three-component reaction con- taining 2-(1,3-dioxo-lH-inden-2(3H)-ylidene)malononitrile resulted in spiro[indene-2,7'-thiazolo[3,2-a]pyridine] derivatives. The three-component reaction of thiazole (benzothiazole), dialkyl but-2-ynedioate, and isatinylidene malononi- triles in toluene at 110-120 ℃ in a sealed tube afforded a mixture of cis/trans-isomers of functionalized di- astereoisomeric spiro[indoline-3,7'-thiazolo[3,2-a]pyridines] and spiro[benzo[4,5]thiazolo[3,2-a]pyridine-3,3'-in- dolines] in good yields. Both cis-isomers and trans-isomers were successfully separated out and fully characterized with spectroscopy and single crystal determination. Under similar conditions, the three-component reaction con- taining 2-(1,3-dioxo-lH-inden-2(3H)-ylidene)malononitrile resulted in spiro[indene-2,7'-thiazolo[3,2-a]pyridine] derivatives.
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2015年第12期1371-1379,共9页 中国化学(英文版)
基金 This work was financially supported by the National Natural Science Foundation of China (No. 21172189) and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We also wanted to give sincerely thanks to the Analysis Center of Yangzhou University for providing all necessary in- struments for characterization of structures.
关键词 multicomponent reaction SPIROOXINDOLE thiazole BENZOTHIAZOLE electron-deficient alkyne malononi-trile multicomponent reaction, spirooxindole, thiazole, benzothiazole, electron-deficient alkyne, malononi-trile
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