New preparative route to hetaryldienes and azadienes

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Tetrazolylacroleins easily available via a four step pathway from 2-aminopyridines proved to be suitable starting compounds for preparation of new tetrazolyldiene systems. Reaction with reagents containing active methylene group gave a series of new dienes, whereas hydroxylamines yielded nitrones. The new dienes underwent cyclizations with electron withdrawn dienophiles to yield tetrazolyl substituted new polycycles, and the nitrones gave fused isoxazolines. The electron demand of the tetrazolyldienes in cycloadditions was interpreted by calculation of frontier orbital energy levels.

Original languageEnglish
Pages (from-to)2287-2307
Number of pages21
Issue number10
Publication statusPublished - Oct 1 2004


ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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