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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

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

Elwood Jessica M L JML Henry Martyn C MC Lopez-Fernandez J Daniel JD Mowat Jenna M JM Boyle Mhairi M Buist Benjamin B Livingstone Keith K Jamieson Craig C

Organic letters 20221216 51

We report the use of <i>N</i>-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 <i>N</i>-acylation of re ...[more]

PMID: 36524745

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