Functionalized tetrazoles as latent active esters in the synthesis of amide bonds

Elwood, Jessica M. L. and Henry, Martyn C. and Lopez-Fernandez, J. Daniel and Mowat, Jenna M. and Boyle, Mhairi and Buist, Benjamin and Livingstone, Keith and Jamieson, Craig (2022) Functionalized tetrazoles as latent active esters in the synthesis of amide bonds. Organic Letters, 24 (51). pp. 9491-9496. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.2c03971)

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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.

ORCID iDs

Elwood, Jessica M. L., Henry, Martyn C., Lopez-Fernandez, J. Daniel, Mowat, Jenna M., Boyle, Mhairi, Buist, Benjamin, Livingstone, Keith and Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272;
CORE (COnnecting REpositories)