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Acetic anhydride to the rescue: Facile access to privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core via the Castagnoli-Cushman reaction

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Abstract Indole-fused cyclic anhydrides earlier deemed unreactive in the Castagnoli-Cushman reaction with imines have been rendered valid participant in this process. The new reaction format involves the use of respective… Click to show full abstract

Abstract Indole-fused cyclic anhydrides earlier deemed unreactive in the Castagnoli-Cushman reaction with imines have been rendered valid participant in this process. The new reaction format involves the use of respective indole-based dicarboxylic acids and in situ cyclodehydration of the latter by acetic anhydride. This finding validates a fundamentally new approach to synthesizing compounds based on the privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core characterized by hitherto undescribed substitution pattern.

Keywords: acetic anhydride; castagnoli cushman; privileged tetrahydropyrazino; reaction; tetrahydropyrazino indole; cushman reaction

Journal Title: Tetrahedron Letters
Year Published: 2018

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