Efficient and convenient synthesis of indazol-3(2H)-ones and 2-aminobenzonitriles

J Comb Chem. 2009 Nov-Dec;11(6):1073-7. doi: 10.1021/cc9001058.

Abstract

A mild, efficient, one-pot protocol for the synthesis of indazole-3(2H)-ones via cyclization of nitro-aryl substrates through low-valent titanium reagent has been described. The method used Triethylamine (TEA) to control pH. Particularly, 2-aminobenzonitriles were synthesized by one step easily. The mechanistic course of the reaction suggests the involvement of an anion leading to an intramolecular cyclization via N-N bond formation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques / methods
  • Crystallography, X-Ray
  • Cyclization
  • Indazoles / chemical synthesis*
  • Indazoles / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Stereoisomerism

Substances

  • Indazoles
  • Nitriles
  • benzonitrile