Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides

Mhairi Boyle, Keith Livingstone, Martyn C. Henry, Jessica M. L. Elwood, J. Daniel Lopez Fernandez, Craig Jamieson

Research output: Contribution to journalLetterpeer-review

7 Citations (Scopus)
41 Downloads (Pure)

Abstract

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.
Original languageEnglish
Pages (from-to)334-338
Number of pages5
JournalOrganic Letters
Volume24
Issue number1
Early online date29 Dec 2021
DOIs
Publication statusPublished - 14 Jan 2022

Keywords

  • amide bond formation
  • rearrangement of nitrile imines
  • N-2-nitrophenyl hydrazonyl bromides

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