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

✍ Scribed by Katritzky, Alan R. ;Wu, Jing ;Kuzmierkiewicz, Wojciech ;Rachwal, Stanislaw

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 406 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419940102

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✦ Synopsis

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

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