Benzhydrylamines via base-mediated intramolecular sp(3) C-arylation of N-benzyl-2-nitrobenzenesulfonamides--advanced intermediates for the synthesis of nitrogenous heterocycles

ACS Comb Sci. 2014 Oct 13;16(10):573-7. doi: 10.1021/co500098y. Epub 2014 Sep 12.


N-Benzyl-2-nitrobenzenesulfonamides underwent base-mediated intramolecular arylation at the benzyl sp(3) carbon to yield benzhydrylamines. The presence of electron withdrawing groups on the aromatic ring of the benzyl group was required to facilitate the C-arylation. Unsymmetrically substituted benzhydrylamines are advanced intermediates toward nitrogenous heterocycles, as exemplified in the syntheses of indazole oxides and quinazolines.

Keywords: C−C bond formation; arylation; benzhydrylamine; heterocycle; indazole oxide; nitrobenzenesulfonamides; quinazoline.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Benzhydryl Compounds / chemistry*
  • Benzyl Compounds / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Indazoles / chemical synthesis
  • Indicators and Reagents
  • Quinazolines / chemical synthesis


  • Alcohols
  • Benzhydryl Compounds
  • Benzyl Compounds
  • Heterocyclic Compounds
  • Indazoles
  • Indicators and Reagents
  • Quinazolines
  • benzhydrylamine