1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction

Org Lett. 2019 Sep 20;21(18):7320-7323. doi: 10.1021/acs.orglett.9b02614. Epub 2019 Sep 3.

Abstract

Easy to perform, functional group tolerant, and short syntheses of the privileged scaffold oxadiazole are highly desired. Here, a metal-free protocol for MCR-based synthesis of 2,5-disubstituted 1,3,4-oxadiazoles via a Ugi-tetrazole/Huisgen sequence was developed. Optimization and scope and limitations of this short and general sequence are described. The reaction was also successfully performed on a gram scale.

Publication types

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

MeSH terms

  • Molecular Structure
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Tetrazoles / chemistry*

Substances

  • Oxadiazoles
  • Tetrazoles
  • 1,3,4-oxadiazole
  • 1H-tetrazole