Facile assembly of fused benzo[4,5]furo heterocycles

J Org Chem. 2008 Apr 4;73(7):2951-4. doi: 10.1021/jo8000595. Epub 2008 Mar 11.

Abstract

A concise synthesis of fused benzo[4,5]furo heterocycles 18 has been developed. Chemo/regioselective Suzuki coupling between 1,2-dihaloarene 17 and alpha-hydroxyphenylboronic acid or ester 20 gives biaryl phenol 19, which then undergoes copper(I) thiophene-2-carboxylate (CuTC)-mediated intramolecular cyclization to afford 18 in good overall yield. This method has broad substrate scope and allows facile assembly of a wide variety of benzo[4,5]furo heterocycles.

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzofurans
  • Heterocyclic Compounds