Issue 47, 2025

Privileged scaffolds on demand: a Passerini-based strategy toward α-ketoamides

Abstract

We report a scalable Passerini-based method for synthesizing α-ketoamides, key medicinal motifs. Using p-hydroxybenzoic acid and ethanol, Mumm rearrangement was interrupted to yield α-hydroxyamides and then oxidized in one pot. The method tolerates diverse substrates, enables gram-scale synthesis and affords inhibitors of human 15-LOX-1, highlighting its biological and synthetic potential.

Graphical abstract: Privileged scaffolds on demand: a Passerini-based strategy toward α-ketoamides

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Article information

Article type
Communication
Submitted
15 Oct 2025
Accepted
13 Nov 2025
First published
14 Nov 2025
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2025,23, 10679-10683

Privileged scaffolds on demand: a Passerini-based strategy toward α-ketoamides

M. Georgoulakis, I. Angelonidis, K. G. Froudas, N. Eleftheriadis and C. G. Neochoritis, Org. Biomol. Chem., 2025, 23, 10679 DOI: 10.1039/D5OB01629K

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