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.

Metadata

Authors/Creators:	Elwood, JML Henry, MC Lopez-Fernandez, JD Mowat, JM Boyle, M Buist, B Livingstone, K https://orcid.org/0000-0002-4169-3056 Jamieson, C
Copyright, Publisher and Additional Information:	© 2022 The Authors. Published by American Chemical Society. This is an open access article under the terms of the Creative Commons Attribution License (CC-BY 4.0), which permits unrestricted use, distribution and reproduction in any medium, provided the original work is properly cited.
Dates:	Published (online): 16 December 2022 Published: 30 December 2022
Institution:	The University of Leeds
Academic Units:	The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Organic Chemistry (Leeds)
Depositing User:	Symplectic Publications
Date Deposited:	05 Apr 2023 08:33
Last Modified:	05 Apr 2023 08:33
Status:	Published
Publisher:	American Chemical Society
Identification Number:	https://doi.org/10.1021/acs.orglett.2c03971
Related URLs:	Dataset