Efficient Synthesis of 1,3,4-Oxadiazoles Conjugated to Thiophene or Furan Rings via an Ethenyl Linker

Abstract

A novel and efficient synthesis of 5-substituted 2-[2-(2-furyl)ethenyl]-1,3,4-oxadiazoles and 2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazoles by cyclocondensation of the appropriate 3-(2-furyl)- and 3-(2-thienyl)acrylohydrazides with triethyl orthoesters in the presence of glacial acetic acid is reported. The formation of symmetrically substituted 2,5-bis[2-(2-furyl)ethenyl]-1,3,4-oxadiazole and 2,5-bis[2-(2-thienyl)ethenyl]-1,3,4-oxadiazole from the corresponding N,N′-diacylhydrazines under the influence of phosphorus oxychloride is also described.

Key words

cyclization - heterocycles - furans - thiophenes - 1,3,4-oxadiazoles

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