In an investigation of the role of the nitrogen atoms in the ring-transformation reactions of nitrogen bridgehead condensed pyrimidinones (1), either the bridgehead or the non-bridgehead nitrogen atom was replaced by a carbon atom. While replacement of the non-bridgehead nitrogen atom did not influence the ring-transformation reaction, replacement of the bridgehead nitrogen atom prevented the rearrangement. Thus, ethyl 1-cyano-6-methyl-4-oxp- 4H-quinolizine-3-carboxylate (10) was transformed into ethyl 8-cyano-5-hydroxy-2-methylquinoline-6-carboxylate (11) at 250 °C. X-Ray crystallographic analysis confirms the structure of (11): monoclinic system with a = 11.385(1), b = 11.102(1), c = 10.191(2)Å, space group P2 1/n, Z = 4, Dc = 1.36 g cm-3, R = 0.043. The quinoline (11) gave 5-ethoxy-2-methylquinoline-8-nitrile (12) at 260 °C.
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - Dec 1 1984|
ASJC Scopus subject areas