Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes

J Org Chem. 2011 Nov 4;76(21):8840-51. doi: 10.1021/jo201605v. Epub 2011 Oct 12.

Abstract

A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrocarbons, Halogenated / chemistry
  • Indazoles / chemical synthesis*
  • Indazoles / chemistry
  • Molecular Structure
  • Palladium / chemistry
  • Stereoisomerism
  • Sydnones / chemistry*

Substances

  • Hydrocarbons, Halogenated
  • Indazoles
  • Sydnones
  • Palladium