Facile synthesis of 1,3,4-benzotriazepines and 1-arylamide-1H-indazoles via palladium-catalyzed cyclization of aryl isocyanates and aryl hydrazones under microwave irradiation

Org Biomol Chem. 2010 Nov 7;8(21):4827-30. doi: 10.1039/c0ob00021c. Epub 2010 Sep 8.

Abstract

A strategy involving palladium-catalyzed cyclization of halo-phenyl hydrazones and aryl isocyanates provides a convenient approach to the synthesis of 1,3,4-benzotriazepines (4) or 1-arylamide-1H-indazoles (5) in good isolated yields. Microwave irradiation was found to afford high reaction efficiency, while the choice of halophenyl hydrazone had an effect on the pathway of the reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzazepines / chemical synthesis*
  • Benzazepines / chemistry
  • Catalysis
  • Cyclization
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Indazoles / chemical synthesis*
  • Indazoles / chemistry
  • Isocyanates / chemical synthesis
  • Isocyanates / chemistry*
  • Microwaves
  • Palladium / chemistry*

Substances

  • Benzazepines
  • Hydrazones
  • Indazoles
  • Isocyanates
  • Palladium