Unusual Lewis-acid catalyzed formal (3+3)-cycloaddition of azomethine imines and nitrones to N-vinylpyrroles

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• 作者：Mariia M. Efremova^a ; Rafael R. Kostikov^a ; Alexander V. Stepakov^a ; Taras L. Panikorovsky^a ; Victoriya S. Shcherbakova^b ; Andrey V. Ivanov^b ; Alexander P. Molchanov^a ; ^{a.molchanov@spbu.ru}
• 关键词：Pyrroles ; (3+3)-cycloadditiones ; Nitrones ; Azomethine imines ; Catalysis
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：9 February 2017
• 年：2017
• 卷：73
• 期：6
• 页码：671-680
• 全文大小：820 K
• 卷排序：73

文摘

The addition of Lewis acids change the reaction mechanism of the cycloaddition of N-vinylpyrroles with azomethine imine and C,N-diarylnitrones. The formal (3+3)-cycloaddition is observed instead of (3+2)-dipolar cycloaddition, which take place in the absence of catalysts. This unusual (3+3)-cycloaddition leads to heterocyclic compounds with pyrazolo[1,2-a]pyrrolo[1,2-d][1,2,4]triazine- and pyrrolo[2,1-d][1,2,5]oxadiazine cores, which are difficultly achievable by other methods.