An unusual Fischer indole synthesis with 4-keto acids: an indole incorporating the terminal hydrazine nitrogen

…, S Karady, EG Corley, AV Lovell, I Shinkai

Index: Conn, Robin S. Eichen; Douglas, Alan W.; Karady, Sandor; Corley, Edward G.; Lovell, Alfred V.; Shinkai, Ichiro Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2908 - 2913

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Citation Number: 8

Abstract

During preparation of a pharmaceutically active, N-benzylated indole derivative from 4-keto acid and N1-benzylated phenylhydrazine precursors, the N-unsubstituted indole analogue arose as a significant byproduct. The proportion of debenzylated indole was greater with a- alkylated rather than straight-chain keto acids and the byproduct was fully suppressed when a keto ester was substituted for the keto acid. The benzylic group was shown to have ...