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Paper | Regular issue | Vol 51, No. 9, 1999, pp.2093-2102
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8603
Synthesis of 3-(4-Aryl-3-cyano-2-methoxypyridin-6-yl)tropolones by the Reactions of 3-Cinnamoyltropolones with Malononitrile

Dao-Lin Wang and Kimiaki Imafuku*

*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan


3-Cinnamoyltropolones (1a-k) reacted with malononitrile in methanol in the presence of sodium hydroxide or methoxide to give 2-(4-aryl-3-cyano-2-methoxypyridin-6-yl)tropolones (2a-k) via Michael addition and cydization. The reactions in the presence of ethoxide or 1-propoxide afforded the corresponding 2-ethoxy- and 2-(l-propoxy)pyridine derivatives (3a,b), respecvely. 3-(3-Heterocycle-substituted 2-propenoyl)tropolones (6a-d) gave the pyridines (7a-d) having both tropolone and heteocyclic ring.