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Paper | Regular issue | Vol 89, No. 4, 2014, pp.995-1007
Published online, 14th March, 2014
DOI: 10.3987/COM-14-12952
New 1,2- and 1,3-Aza-Ylides of 3-Amino-2-substituted-1H-isoindoles

Hatem A. Abdel-Aziz,* Tilal Elsaman, Khalid A. Al-Rashood, and Hoong-Kun Fun

*Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh-11451, Saudi Arabia

Abstract

The reaction of 2-(bromomethyl)benzonitrile (5) with hydrazides 6a-f or heterocyclic amines 14a-c gave isoindolium bromides 7a-f and 15a-f, respectively. Deprotonation of the latter salts afforded the 1,2-aza-ylides 8a-f and 1,3-aza-ylides 16a-c instead of the analogous imines 9a-f or 17a-c, respectively. Single crystal X-ray and NMR analyses confirmed the stable ylide structures of 8a-f and 16a-c and established the presence of a complete benzenoid unit in the isoindole moiety, in both the solid state and solution phase.