Experimental and theoretical studies on some new pyrrol‐2,3‐diones formation

Abstract

Abstract4‐Benzoyl‐5‐phenyl‐2,3‐furandione (1) reacts with asymmetric disubstituted urea derivatives like 1,1‐dimethylurea (2a) and 1,1‐diethylurea (2b) by the elimination of a H2O molecule to give the 4‐benzoyl‐1‐(N,N‐dialkylcarbamyl)‐5‐phenyl‐2,3‐pyrroldiones 3a and 3b. The structures of 3a,b were determined by the 13C NMR, 1H NMR, IR spectroscopic data and elemental analyses. The electronic structures of the reactants, their transition states, intermediate states, and final products of the reactions were investigated on the basis of AM1 and ab initio (DFT) methods. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 15:9–14, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10204