A novel selective route to 1‐substituted benzotriazoles via lithiation of simple 1‐alkylbenzotriazoles

Abstract 1‐Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1‐substituted benzotriazoles 5. Other 1‐(n‐alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N‐1 atom. On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. magnified image