Nitrogen bridgehead compounds, part 68. Studies on quinolizine derivatives. Part 2. Synthesis of 1,3‐disubstituted‐4H‐quinolizine derivatives

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

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Abstract

Quinolizine compounds 1 and 2 or their monocyclic tautomers 3 and 4 have been synthesized using 2‐pyri‐dineacetic acid derivatives 6a, b, A, B and ethoxymethylenemalonic acid derivatives 7a, b, c in base catalyzed or thermic reaction. In the 6‐unsubstituted series, both the 4‐oxo and 4‐imino derivatives could have been obtained, in the 6‐substituted series, however the 4‐oxo ones only, whereas instead of the 4‐imino derivatives, their monocyclic tautomers 3, 4 have been isolated. In the 6‐unsubstituted series, the primarily formed 4‐imino compounds have been rearranged into 4‐oxo ones under stronger conditions. The structure of the isolated compounds have been proved by ultraviolet, infrared and 1H nmr spectra, that of 3B=C by X‐ray analysis as well.

Original languageEnglish
Pages (from-to)645-650
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume24
Issue number3
DOIs
Publication statusPublished - Jan 1 1987

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ASJC Scopus subject areas

  • Organic Chemistry

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