Issue 48, 2016

Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors

Abstract

A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.

Graphical abstract: Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors

Supplementary files

Article information

Article type
Communication
Submitted
20 Oct 2016
Accepted
21 Nov 2016
First published
22 Nov 2016

Org. Biomol. Chem., 2016,14, 11353-11356

Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors

A. Angeli, T. S. Peat, G. Bartolucci, A. Nocentini, C. T. Supuran and F. Carta, Org. Biomol. Chem., 2016, 14, 11353 DOI: 10.1039/C6OB02299E

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