The Journal of Organic Chemistry

Phase-transfer alkylation of heterocycles in the presence of 18-crown-6 and potassium tert-butoxide

WC Guida, DJ Mathre

Index: Guida, Wayne C.; Mathre, David J. Journal of Organic Chemistry, 1980 , vol. 45, # 16 p. 3172 - 3176

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Citation Number: 106

Abstract

It has been found that the N-alkylation of heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen can be accomplished in diethyl ether via a phase- transfer process in which 18-crown-6 is employed as the catalyst and potassium tert- butoxide is employed as the base. In this manner, pyrrole (11, indole (21, pyrazole (3), imidazole (4), benzimidazole (5), benzotriazole (6), carbazole (7), and methyl indole-3- ...