Table of Contents
ISRN Organic Chemistry
Volume 2011, Article ID 469453, 5 pages
http://dx.doi.org/10.5402/2011/469453
Research Article

New Way to Substitute Tetracyanocyclopropanes: One-Pot Cascade Assembling of Carbonyls and Malononitrile by the Only Bromine Direct Action

Homolytic Reactions Research Laboratory, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia

Received 12 April 2011; Accepted 24 May 2011

Academic Editors: A. Hajra, A. Iuliano, J. Perez-Castells, and A. Schlapbach

Copyright © 2011 Anatolii N. Vereshchagin 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

The new type of the chemical cascade reaction was found: formation of cyclopropanes from carbonyl compounds and CH acid by the only bromine direct action. The action of aqueous bromine on the carbonyl compounds and malononitrile in EtOH-H2O solutions in the presence of NaOAc results in the formation of 3-substituted 1,1,2,2-tetracyanocyclopropanes in 48–93% yields. The latter are well-known precursors for the different bicyclic heterosystems, among them those containing cyclopropane ring and those possessing different types of pharmacological activity.