Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones

J Org Chem. 2018 Aug 17;83(16):9522-9529. doi: 10.1021/acs.joc.8b01249. Epub 2018 Jun 27.

Abstract

A wide range of azolo[1,3,5]triazines were obtained by Rh(III)-catalyzed annulation of N-azolo imines and dioxazolones. The reaction proceeds by the first catalytic C-H amidation of an imidoyl C-H bond followed by cyclodehydration. Good yields were obtained for N-azolo imines derived from aminoazoles and aromatic and heteroaromatic aldehydes. A range of dioxazolone amidating reagents were employed to introduce aryl, heteroaryl, and alkyl substituents. The reaction was also performed with a benchtop setup at 1 mmol scale using microwave heating.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Imines / chemistry*
  • Oxazolone / chemistry*
  • Rhodium / chemistry*
  • Triazines / chemical synthesis*
  • Triazines / chemistry*

Substances

  • Imines
  • Triazines
  • Oxazolone
  • Rhodium