Synthetic Utility of tert-Butyl Azidoacetate on the Hemetsberger-Knittel Reaction. Synthetic Studies of Indoles and Related Compounds. Part 47.

…, S Morohoshi, M Mitsuhashi, Y MURAKAMI

Index: Kondo, Kazuhiro; Morohoshi, Sachiko; Mitsuhashi, Masaharu; Murakami, Yasuoki Chemical and Pharmaceutical Bulletin, 1999 , vol. 47, # 9 p. 1227 - 1231

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Citation Number: 24

Abstract

The synthetic utility of tert-butyl azidoacetate (7) on the Hemetsberger-Knittel reaction is described. The following two findings are disclosed by using tert-butyl azidoacetate (7): i) in the first step for the synthesis of ethyl indole-2-carboxylate 4, the aldol reaction of less reactive aldehydes 1a, b was improved greatly; ii) tert-butyl indole-2-carboxylate 10 becomes readily available from aldehydes.