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Journal of Chemistry
Volume 2016, Article ID 1504682, 5 pages
http://dx.doi.org/10.1155/2016/1504682
Research Article

An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting from trans-4-Hydroxy-L-proline

Laboratoire de Chimie, URCOM, EA 3221, FR CNRS 3038, Normandie Université, Université du Havre, UFR Sciences et Techniques, 25 rue Philippe Lebon, 76058 Le Havre Cedex, France

Received 2 November 2015; Accepted 29 December 2015

Academic Editor: Marco Radi

Copyright © 2016 Sébastien Comesse and Adam Daïch. 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

The straightforward synthesis of pyrrolo[3,4-b]quinolone and pyrrolo[3,2-b]quinolone backbones, which can be found in molecules exhibiting anticancer activities, is presented. The key step of the process is an efficient and unprecedented Friedländer condensation between an oxoproline carbamate, obtained in 3 steps and good yield starting from commercially available and relatively cheap trans-4-hydroxy-L-proline, and various 2-amino-substituted carbonyl derivatives. It was demonstrated that the formation of the two possible regioisomers was fully triggered by both the R substituent onto the 2-amino-substituted carbonyl compounds and the ester function onto the oxoproline carbamate. Thus, in some cases, a complete regiocontrol for the Friedländer reaction could be attained.