Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2

J Org Chem. 2009 Jan 16;74(2):921-4. doi: 10.1021/jo802076k.

Abstract

Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoximes, DMAD, and bromine are described, which afford the unexpected isoquinoline-based azomethine ylides in good to excellent yields. The products could be further elaborated via palladium-catalyzed cross-coupling reactions to generate highly functionalized isoquinoline-based stable azomethine ylides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Bromine / chemistry*
  • Catalysis
  • Cyclization
  • Isoquinolines / chemistry
  • Oximes / chemistry*
  • Transition Elements / chemistry

Substances

  • Alkynes
  • Isoquinolines
  • Oximes
  • Transition Elements
  • acetylenedicarboxylic acid dimethyl ester
  • isoquinoline
  • Bromine