Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.

ABSTRACT: The targeted cleavage of the C-N bonds of alkyl primary amines in sustainable compounds of biomass according to a metal-free pathway and the conjunction of nitrogen in the synthesis of imidazo[1,5-a]pyridines are still highly challenging. Despite tremendous progress in the synthesis of imidazo[1,5-a]pyridines over the past decade, many of them can still not be efficiently prepared. Herein, we report an anomeric stereoauxiliary approach for the synthesis of a wide range of imidazo[1,5-a]pyridines after cleaving the C-N bond of d-glucosamine (α-2° amine) from biobased resources. This new approach expands the scope of readily accessible imidazo[1,5-a]pyridines relative to existing state-of-the-art methods. A key strategic advantage of this approach is that the α-anomer of d-glucosamine enable

SUBMITTER: Zeng K 

PROVIDER: S-EPMC9325398 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature