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

Boyle, Mhairi and Livingstone, Keith and Henry, Martyn C. and Elwood, Jessica M. L. and Lopez Fernandez, J. Daniel and Jamieson, Craig (2022) Amide bond formation via the rearrangement of nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides. Organic Letters, 24 (1). pp. 334-338. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.1c03993)

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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.

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