Nitrogen bridgehead compounds. Part 41. Ring transformation of nitrogen bridgehead ring systems

István Hermecz, Zoltán Mészáros, Kálmán Simon, László Szabó, Zoltán Pál

Research output: Contribution to journalArticle

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Abstract

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.

Original languageEnglish
Pages (from-to)1795-1798
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - Dec 1 1984

ASJC Scopus subject areas

  • Chemistry(all)

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