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

Jessica M. L. Elwood, Martyn C. Henry, J. Daniel Lopez-Fernandez, Jenna M. Mowat, Mhairi Boyle, Benjamin Buist, Keith Livingstone, Craig Jamieson

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)
40 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)9491-9496
Number of pages6
JournalOrganic Letters
Volume24
Issue number51
Early online date16 Dec 2022
DOIs
Publication statusE-pub ahead of print - 16 Dec 2022

Keywords

  • latent active esters
  • amide bonds
  • pharmaceutical agents

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