Synthesis of some novel polyaza fused heterocyclic compounds

✍ Scribed by Fathy M. Abdelrazek; Nadia H. Metwally; Nazmi A. Kassab; Nehal A. Sobhy; Peter Metz; Anna Jaeger

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 184 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.329

✦ Synopsis

Abstract

magnified image 2‐(1‐Aryl‐ethylidene)‐malononitriles 1a, 1b, 1c, 1d undergo self dimerization in ethanol catalyzed by sodium ethoxide to afford 2‐[4,6‐diaryl‐3‐cyano‐6‐methyl‐5,6‐dihydropyridin‐2(1__H__)‐ylidene]‐malononitrile derivatives 3a, 3b, 3c, 3d respectively. The structure of the dimer was elucidated by X‐ray crystallography and a plausible mechanism for its formation is depicted. Compound 3a couples with arene diazonium salts 4a, 4b, 4c, 4d to afford the hydrazo derivatives 5a, 5b, 5c, 5d and reacts with hydrazine hydrate and phenylhydrazine 6a, 6b to afford the pyrazolo[3,4‐h][1,6]naphthyridine derivatives7a, 7b and with urea and thiourea 8a, 8b to afford the pyrimido[4,5‐h][1,6]naphthyridine derivatives 9a, 9b, respectively. J. Heterocyclic Chem., (2010).