Tetrahedron letters

A novel synthesis of 3-cyanoindoles and a new route to indole-3-carboxylic acid derivatives

J Garcia, R Greenhouse, JM Muchowski, JA Ruiz

Index: Garcia, Josefina; Greenhouse, Robert; Muchowski, Joseph M.; Ruiz, Jose Antonio Tetrahedron Letters, 1985 , vol. 26, # 15 p. 1827 - 1830

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Citation Number: 13

Abstract

Abstract 2-Alkyl-3-cyanoindoles are obtained when 1-alkylmethyl-2-chloro-(or 2- phenylsulfonyl)-3-phenylsulfonylindoles are reacted with excess azide ion (90/DMF). The reaction is considered to occur by a fragmentation recombination process in which the Schiff's base 12 is of central importance. This proposal is supported by the formation of 2- substituted indole-3-carboxylates 17 from aldehydes and the α-phenylsulfonyl-o- ...

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