Selective synthesis and cycloaddition reactions of new azomethine imines containing a 1,2,4-triazine ring

Csilla Gróf, Gábor Hegedus, Zsuzsanna Riedl, György Hajós, Orsolya Egyed, Antal Csámpai, Veronika Kudar, Branko Stanovnik

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5 Citations (Scopus)

Abstract

The reactions of 4,5-dihydro[1,2,4]triazolo[3,4-c]benzo[1,2,4]-triazines with aromatic aldehydes gave stable iminium salts which were deprotonated to give new azomethine imines. These new mesomeric betaines underwent 1,3-dipolar cyclization reactions to yield new tetra- and pentacyclic heterocycles. X-ray analysis and decoupling NMR experiments unambiguously supported the fact that these transformations are regioselective and that the iminium moieties were formed at the N-5 atom in each case.

Original languageEnglish
Pages (from-to)3553-3561
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
Publication statusPublished - Aug 12 2005

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Keywords

  • 1,3-Dipolar cycloaddition
  • Azomethine imine
  • Mesomeric betaine
  • Regioselectivity
  • Solvatochromism

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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