Journal
TETRAHEDRON
Volume 67, Issue 44, Pages 8502-8508Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.09.018
Keywords
1,1 '-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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Funding
- State Committee of Scientific Research [0167/B/H03/2010/38]
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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