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

✍ Scribed by Abdellatif M. Salah Eldin

Book ID: 102232208
Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 84 KB
Volume: 14
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.10199

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✦ Synopsis

Abstract

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. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:612–616, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10199

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