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

Agnieszka Kudelko; Karolina Jasiak

doi:10.1055/s-0033-1338454

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(14): 1950-1954
DOI: 10.1055/s-0033-1338454

paper

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

Agnieszka Kudelko*

Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland Fax: +48(32)2371021 eMail: Agnieszka.Kudelko@polsl.pl

,

Karolina Jasiak

Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, 44100 Gliwice, Poland Fax: +48(32)2371021 eMail: Agnieszka.Kudelko@polsl.pl

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Abstract

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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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Referenzen

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