Sc(OTf)3-Mediated One-Pot Synthesis of 3,4-Disubstituted 1 H-Pyrazoles and 3,5-Disubstituted Pyridines from Hydrazine or Ammonia with Epoxides

J Org Chem. 2022 Dec 16;87(24):16820-16828. doi: 10.1021/acs.joc.2c02544. Epub 2022 Dec 7.

Abstract

Here, we report the synthesis of 3,4-disubstituted 1H-pyrazoles and 3,5-disubstituted pyridines from the reaction of epoxides with hydrazine and ammonia, respectively. Both reactions utilize Sc(OTf)3 as a Lewis acid. The pyrazole synthesis utilizes N-bromosuccinimide to convert the intermediate pyrazolines to the pyrazoles, whereas the pyridine synthesis utilizes FeCl3 as a cocatalyst.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Ammonia*
  • Epoxy Compounds
  • Hydrazines
  • Pyrazoles
  • Pyridines*

Substances

  • pyrazole
  • Pyridines
  • Ammonia
  • Epoxy Compounds
  • Pyrazoles
  • hydrazine
  • Hydrazines