Formation of 4,5,6,7-tetrahydroisoindoles by palladium-catalyzed hydride reduction

Duen Ren Hou, Ming Shiang Wang, Ming Wen Chung, Yih Dar Hsieh, Hui Hsu Gavin Tsai

研究成果: 雜誌貢獻期刊論文同行評審

22 引文 斯高帕斯(Scopus)

摘要

(Chemical Equation Presented) Substituted 1,3-dihydro-2H-isoindoles (2, isoindolines) were prepared and subjected to palladium-catalyzed formate reduction. Alkyl isoindolines were reduced to 4,5,6,7-tetrahydro-2H-isoindoles (1). Only partial reduction was observed for 5-methoxyisoindoline, and 4-methoxy-, 5-carbomethoxy-, amino-, and amidoisoindolines were inert to the reaction. Halogen-substituted isoindolines were dehalogenated and reduced to 4,5,6,7-tetrahydro-2H-isoindoles. Isoindole 24 was also reduced to a mixture of an isoindoline and a 4,5,6,7-tetrahydro-2H-isoindole. In contrast, 2,3-dihydro-1H-indoles 21 underwent dehydrogenation to give thermodynamically stable indoles. Theoretical calculations show the significant difference in aromaticity between isoindoles and indoles, corresponding to the observed differences in reactivities. Tetrahydro-2H-isoindoles 1 were oxidized to 4,5,6,7-tetrahydroisoindole-1,3-diones in the presence of NBS and air.

原文???core.languages.en_GB???
頁(從 - 到)9231-9239
頁數9
期刊Journal of Organic Chemistry
72
發行號24
DOIs
出版狀態已出版 - 23 11月 2007

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