Base-mediated intramolecular C- and N-arylation of N,N-disubstituted 2-nitrobenzenesulfonamides: advanced intermediates for the synthesis of diverse nitrogenous heterocycles

ACS Comb Sci. 2014 Sep 8;16(9):500-5. doi: 10.1021/co5000739. Epub 2014 Aug 8.

Abstract

Structural and electronic features that facilitate and direct the intramolecular C- and N-arylation of 2-alkyl-2-{[N-(benzyl)-2-nitrophenyl]sulfonamido}acetic acid esters and amides were examined. The substitution pattern and amino acid carboxy-terminal functionality determined the arylation position. C/N-arylated products represent advanced intermediates for combinatorial synthesis of diverse nitrogenous heterocycles, including indazoles, quinazolinones, quinoxalinones, and 3-amino-2-oxindoles.

Keywords: C−C bond formation; arylation; diversity-oriented synthesis; heterocycle; nitrobenzenesulfonamides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Nitrogen / chemistry*
  • Sulfonamides / chemistry*

Substances

  • Heterocyclic Compounds
  • Nitro Compounds
  • Sulfonamides
  • Carbon
  • Nitrogen