Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides

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23 Citations (Scopus)

Abstract

(Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4π electrocyclization, and ring expansion.

Original languageEnglish
Pages (from-to)6470-6472
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number48
DOIs
Publication statusPublished - 2011 Nov 30

Keywords

  • Alkyne
  • Electrocyclization
  • Oxime
  • Pyridine
  • Skeletal rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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