Zinc-Mediated Facile and Efficient Chemoselective S-Alkylation of 5-Aryl-1,3,4-oxadiazole-2-thiols in the Absence of Base

Abstract

Zinc-mediated facile and efficient chemoselective S-alkylation of 5-aryl 1,3,4-oxadiazole-2-thiols in the presence of a catalytic amount of tetra butyl ammonium iodide was described. The reaction was performed under neutral conditions. The chemoselectivity of the alkylation was confirmed by NMR spectroscopy and x-ray crystallography.

Keywords:

• Alkylation
• chemoselectivity
• oxadiazole
• piperazines
• zinc

ACKNOWLEDGMENT

R. V. R., K. R. R., and N. R. R are grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for the research fellowships.

Notes

^a All products were characterized by ¹H NMR, ESI-HRMS, and IR spectroscopy.

^b Isolated yields after column chromatography.