Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives

J Org Chem. 2013 Feb 15;78(4):1583-8. doi: 10.1021/jo302696y. Epub 2013 Jan 24.

Abstract

A regiospecific synthesis of multifunctional pyrazoleshas been developed from a cascade process triggered by Rh(II)-catalyzed dinitrogen extrusion from enol diazoacetates with vinylogous nucleophilic addition followed by Lewis acid catalyzed cyclization and aromatization.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Azo Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Hydrazones / chemistry*
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Stereoisomerism

Substances

  • Azo Compounds
  • Hydrazones
  • Pyrazoles
  • pyrazole