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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Authors: | Maria Chizhova Olesya Khoroshilova Dmitry Darin Mikhail Krasavin |
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Institution: | Saint Petersburg State University, Saint Petersburg 199034, Russian Federation |
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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 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-tetrahydropyrazino1,2-a]indole core characterized by hitherto undescribed substitution pattern. |
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Keywords: | Castagnoli-Cushman reaction Dicarboxylic acids Acetic anhydride Vicinal coupling constants |
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