Table of Contents
ISRN Organic Chemistry
Volume 2012, Article ID 281642, 5 pages
http://dx.doi.org/10.5402/2012/281642
Research Article

N-Aryl Lactams by Regioselective Ozonation of N-Aryl Cyclic Amines

Department of Environmental Sciences, University of Milano-Bicocca, Piazza della Scienza 1, 20126 Milano, Italy

Received 20 August 2012; Accepted 11 September 2012

Academic Editors: R. Pohl, G. Sekar, and H. Wang

Copyright © 2012 Francesco Saliu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Ozonation of N-aryl-cyclic amines in organic solvents gave N-aryl-lactams regioselectively. In particular, 4-(4-aminophenyl)-morpolin-3-one, a key intermediate in the preparation of factor Xa inhibitors, was obtained in fair yields. The method represents an alternative approach for the lactamization of tertiary N-arylic substrates and is based on a “metal-free” introduction of the carbonyl function into the heterocyclic ring.