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Note | Regular issue | Vol 78, No. 8, 2009, pp.2067-2076
Published online, 3rd April, 2009
DOI: 10.3987/COM-09-11685
Alkylheteroaromatic-carbonitriles as Building Blocks in Heterocyclic Synthesis: Synthesis of Ethyl 1-Substituted 5-Cyano-4-methyl-6-oxopyridine-3-carboxylates; Versatile Precursors for Polyfunctionally Substituted Isoquinolines and Pyrido[3,4-c]pyridine

Khaled D. Khalil, Hamad M. Al-Matar,* and Mohamed H. Elnagdi

*Department of Chemistry, Faculty of Science, Kuwait University, Safat 13060, P.O. Box 5969, Kuwait


The title compounds were prepared via reacting diethyl 2-cyano-4-dimethylamino-methylene-3-methylpent-2-enedioic acid 2 with hydrazine hydrate and with ethyl amine. The formed pyridones 3a condensed with dimethylformamide dimethyl acetal to yield the corresponding enamine 4 that could be cyclised into the pyrido[3,4-c]pyridine 5 by reflux in acetic acid in presence of ammonium acetate. The reaction of 3a with elemental sulfur afforded the thienopyridine 6 that reacted readily with electron poor olefins and acetylenes to yield isoquinolines 8, 10 and 11. Compound 3a reacted with benzylidene-malononitrile to yield the isoquinoline 14.