Journal of Organic Chemistry p. 3172 - 3176 (1980)
Update date:2022-08-16
Topics:
Guida, Wayne C.
Mathre, David J.
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 (1), indole (2), pyrazole (3), imidazole (4), benzimidazole (5), benzotriazole (6), carbazole (7), and methyl indole-3-acetate (8) can be successfully alkylated.The procedure is convenient and mild and generally gives rise to exclusive N-alkylation.
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