Ring-closure reactions of ortho-vinyl-tert-anilines and (Di)aza-heterocyclic analogues via the tert-amino effect: Recent developments

Péter Mátyus, Olivér Éliás, Pál Tapolcsányi, Ágnes Polonka-Bálint, Beáta Halász-Dajka

Research output: Contribution to journalReview article

137 Citations (Scopus)

Abstract

One version of the tert-amino effect operating in tert-anilines possessing an ortho-vinyl substituent affords a fused tetrahydropyridine ring by an isomerization process with the formation of a new carbon-carbon bond between the vinyl and tert-amino moieties. Since its discovery in 1984, this type of cyclization has been efficiently used for the construction of fused-ring systems. However, it has been found that the electron-deficient heterocyclic analogues of tert-anilines, such as diazines, may undergo isomerization at considerably lower reaction rates and, as a consequence, their reactions may require harsh conditions. Recent synthetic studies have indicated that the rate and yield may be improved by incorporating the β-vinylic carbon atom into an electron-deficient ring and/or buttressing the tert-amino group, and/or performing the reaction by means of microwave irradiation.

Original languageEnglish
Pages (from-to)2625-2639
Number of pages15
JournalSynthesis
Issue number16
DOIs
Publication statusPublished - Aug 17 2006

Keywords

  • Heterocycles
  • Isomerization
  • Microwave-assisted synthesis
  • Ring closure
  • Spiro compounds
  • Substituent effects
  • tert-amino effect

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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