A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazole

Org Lett. 2007 May 10;9(10):1875-8. doi: 10.1021/ol070340q. Epub 2007 Mar 14.

Abstract

A novel two-step synthesis of substituted 2-formylpyrroles is described. Aldol adducts of ketones and 4-formyloxazole undergo a dehydration/oxazole hydrolysis/cyclization cascade on sequential treatment with MsCl/Et3N and aqueous NaOH to yield 5-substituted and 4,5-disubstituted 2-formylpyrroles. The methodology was extended to an N-benzyl thiazolium salt.

MeSH terms

  • Formates / chemistry*
  • Hydroxylation
  • Ketones / chemistry*
  • Molecular Structure
  • Oxazoles / chemistry*
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*

Substances

  • 4-formyloxazole
  • Formates
  • Ketones
  • Oxazoles
  • Pyrroles
  • formic acid