Synthesis of 3-(4-aryl-3-cyano-2-methoxypyridin-6-yl)tropolones by the reactions of 3-cinnamoyl-tropolones with malononitrile

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-metho xypyridin-6-yl)tropolones (2a-k) via Michael addition and cyclization. The reactions in the presence of ethoxide or 1-propoxide afforded the correspon ding 2-ethoxy- and 2-(1-propoxy)pyridine derivatives (3a,b), respectively. 3-(3-Heterocycle-substituted 2-propenoyl)tropolones (6a-d) gave the pyridin es (7a-d) having both tropolone and heteocyclic ring.