The synthesis of bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides and other related 1,3,4-oxadiazoles from 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters |
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Authors: | Agnieszka Kudelko |
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Institution: | Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Ul. Krzywoustego 4, PL-44101 Gliwice, Poland |
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Abstract: | Reactions of symmetrical 1,1′-diphenylthiodiacetic acid dihydrazide and triethyl orthoesters in the presence of catalytic amount of glacial acetic acid resulted in the formation of three heterocyclic products: the appropriate bis(1,3,4-oxadiazol-2-yl-phenylmethyl) sulfides, 2-benzyl-1,3,4-oxadiazoles and 2-benzoyl-1,3,4-oxadiazoles. The presence of the latter two compounds is connected with carbon-sulfur fission in the molecule of the starting hydrazide. The identity of the unexpected fission products was confirmed by parallel syntheses of the model 1,3,4-oxadiazoles from phenylacetic acid hydrazide and 2-hydroxymethyl-1,3,4-oxadiazole derivatives. |
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Keywords: | 1 1&prime -Diphenylthiodiacetic acid dihydrazide Bis(1 3 4-oxadiazol-2-yl-phenylmethyl) sulfides 2-Benzyl-1 3 4-oxadiazoles 2-Benzoyl-1 3 4-oxadiazoles Carbon-sulfur fission Oxidation |
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