Carbon dioxide: A reagent for the protection of nucleophilic centres and the simultaneous activation of alternative locations to electrophilic attack.: Part I. A new …

AR Katritzky, K Akutagawa

Index: Katritzky, By Alan R.; Akutagawa, Kunihiko Tetrahedron Letters, 1985 , vol. 26, # 48 p. 5935 - 5938

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Citation Number: 157

Abstract

Abstract Indole was converted into several 2-substituted derivatives by using carbon dioxide both for N-protection and to give an intermediate carbanion stabilizing group. t-Butyllithium was used as a lithiating agent at the alpha-carbon atom of the indole enamino group. The resulting 2-substituted indole-1-carboxylic acids underwent smooth thermal decarboxylation under mild conditions. Alternatively, with longer reaction times the protecting group is lost ...