Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds.

ABSTRACT: We report the use of N-2,4-dinitrophenyltetrazoles as latent active esters (LAEs) in the synthesis of amide bonds. Activating the tetrazole generates an HOBt-type active ester without the requirement for exogenous coupling agents. The methodology was widely applicable to a range of substrates, with up to quantitative yields obtained. The versatility and functional group tolerance were exemplified with the one-step synthesis of various pharmaceutical agents and the N-acylation of resin-bound peptides.

SUBMITTER: Elwood JML 

PROVIDER: S-EPMC9806851 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature