1,7-Electrocyclizations of azomethine ylides

Scope and synthetic aspects

Miklós Nyerges, J. Tóth, Paul W. Groundwater

Research output: Contribution to journalArticle

39 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

Fingerprint

Cycloaddition
Nitrogen
Electrons
azomethine

Keywords

  • Azomethine ylides
  • Electrocyclization
  • Heterocycles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

1,7-Electrocyclizations of azomethine ylides : Scope and synthetic aspects. / Nyerges, Miklós; Tóth, J.; Groundwater, Paul W.

In: Synlett, No. 9, 11.05.2008, p. 1269-1278.

Research output: Contribution to journalArticle

Nyerges, Miklós ; Tóth, J. ; Groundwater, Paul W. / 1,7-Electrocyclizations of azomethine ylides : Scope and synthetic aspects. In: Synlett. 2008 ; No. 9. pp. 1269-1278.
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