Reaction between 4-oxoalkane-1,1,2,2-tetracarbonitriles and morpholine: regioselective synthesis of 5-amino-2-(morpholin-4-yl)-3-(2-oxoalkyl)-3H-pyrrol-3,4-dicarbonitriles

A new approach to the regioselective synthesis of polyfunctional 3H-pyrroles from 4-oxoalkane-1,1,2, 2-tetracarbonitriles is described. 5-Amino-3-(2-aryl-2-oxoethyl)-3H-pyrrol-3,4-dicarbonitriles are prepared from 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles. Diastereomeric 5-amino-2-morpholin-4yl-3-(2-oxocyclohexyl)-3H-pyrrole-3,4-dicarbonitriles were obtained from 1-(2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonitriles. (C) 2011 Elsevier Ltd. All rights reserved.