A NOVEL SELECTIVE ROUTE TO 1-SUBSTITUTED BENZOTRIAZOLES VIA LITHIATION OF SIMPLE 1-ALKYLBENZOTRIAZOLES

1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or L DA at the methyl group to 4 and the subsequent reaction with various e lectrophiles 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 seconda ry alkyl groups on the N-1 atom. On standing in the absence of electro philes, all the lithium derivatives decompose to afford complex mixtur es.