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

[Image: see text] 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...

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Autores principales: Elwood, Jessica M. L., Henry, Martyn C., Lopez-Fernandez, J. Daniel, Mowat, Jenna M., Boyle, Mhairi, Buist, Benjamin, Livingstone, Keith, Jamieson, Craig
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806851/
https://www.ncbi.nlm.nih.gov/pubmed/36524745
http://dx.doi.org/10.1021/acs.orglett.2c03971
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author Elwood, Jessica M. L.
Henry, Martyn C.
Lopez-Fernandez, J. Daniel
Mowat, Jenna M.
Boyle, Mhairi
Buist, Benjamin
Livingstone, Keith
Jamieson, Craig
author_facet Elwood, Jessica M. L.
Henry, Martyn C.
Lopez-Fernandez, J. Daniel
Mowat, Jenna M.
Boyle, Mhairi
Buist, Benjamin
Livingstone, Keith
Jamieson, Craig
author_sort Elwood, Jessica M. L.
collection PubMed
description [Image: see text] 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.
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spelling pubmed-98068512023-01-03 Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds Elwood, Jessica M. L. Henry, Martyn C. Lopez-Fernandez, J. Daniel Mowat, Jenna M. Boyle, Mhairi Buist, Benjamin Livingstone, Keith Jamieson, Craig Org Lett [Image: see text] 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. American Chemical Society 2022-12-16 2022-12-30 /pmc/articles/PMC9806851/ /pubmed/36524745 http://dx.doi.org/10.1021/acs.orglett.2c03971 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Elwood, Jessica M. L.
Henry, Martyn C.
Lopez-Fernandez, J. Daniel
Mowat, Jenna M.
Boyle, Mhairi
Buist, Benjamin
Livingstone, Keith
Jamieson, Craig
Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title_full Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title_fullStr Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title_full_unstemmed Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title_short Functionalized Tetrazoles as Latent Active Esters in the Synthesis of Amide Bonds
title_sort functionalized tetrazoles as latent active esters in the synthesis of amide bonds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9806851/
https://www.ncbi.nlm.nih.gov/pubmed/36524745
http://dx.doi.org/10.1021/acs.orglett.2c03971
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