1,7-Electrocyclizations of azomethine ylides: Scope and synthetic aspects

Miklós Nyerges, Judit Tóth, Paul W. Groundwater

Research output: Contribution to journalReview article

43 Citations (Scopus)

Abstract

The 1,3-dipolar cycloaddition of azomethine ylides is a versatile and efficient tool for the construction of five-membered nitrogen heterocycles. When the azomethine ylide is conjugated with double bonds other pericyclic pathways become available, including 1,5- or 1,7-electrocyclizations, with the latter 8π-electron process having only recently emerged as a potentially useful method for the formation of seven-membered heterocycles. Under special structural circumstances, multistep rearrangements can also be observed. In this account, a summary of our work on the exploration and development of 1,7-electrocyclizations of azomethine ylides is presented.

Original languageEnglish
Pages (from-to)1269-1278
Number of pages10
JournalSynlett
Issue number9
DOIs
Publication statusPublished - May 11 2008

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Keywords

  • Azomethine ylides
  • Electrocyclization
  • Heterocycles

ASJC Scopus subject areas

  • Organic Chemistry

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