Pyridazine, oxazine, pyrrole, and pyrrolo[1,2-a]quinazoline derivatives from malononitrile dimer

2-Amino-1,1,3-tricyano-3-bromopropene was obtained from bromination of 2-amino-1,1,3-tricyanopropene (malononitrile dimer) with N-bromosuccinimide. This bromo derivative reacts with hydrazine hydrate, phenyl hydrazine, and hydroxylamine hydrochloride to afford pyridazine and oxazine derivatives, respectively In base-catalyzed reactions with primary aromatic amines and anthranilic acid derivatives, it produces N-aryl pyrrol-3,5-dicarbonitrile and pyrrolo[1,2-a]quinazolin-5-imine, or pyrrolo[1,2-a]quinazolin-5-one derivatives, respectively. The structures of the newly synthesized heterocycles were established on the basis of elemental analyses and spectral data. (C) 2003 Wiley Periodicals, Inc.