Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles

J Org Chem. 2006 Dec 8;71(25):9548-51. doi: 10.1021/jo0618730.

Abstract

A facile and general protocol for the preparation of 2-amino-1,3,4-oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.

MeSH terms

  • Oxazoles / chemical synthesis*
  • Semicarbazides / chemistry*

Substances

  • Oxazoles
  • Semicarbazides