General method for the synthesis of indoles

PG Gassman, TJ Van Bergen, DP Gilbert…

Index: Gassman,P.G. et al. Journal of the American Chemical Society, 1974 , vol. 96, p. 5495 - 5508

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Citation Number: 138

Abstract

Abstract: A new, general method has been developed for the synthesis of indole and its derivatives from anilines and/3-keto sulfides, a-formyl sulfides, or their derivatives. The method involves initial mono-N-chlorination of the aniline with tert-butyl hypochlorite or some other suitable halogenating agent. Addition of the sulfide to the N-chloroaniline gives an azasulfonium salt, which on treatment with mild base produces a sulfur ylide. These ...

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