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Synthesis of 1,3,4-oxadiazoles

Recent Literature

A facile and general protocol for the preparation of 2-amino-1,3,4-oxadiazoles relies on a tosyl chloride/pyridine-mediated cyclization of thiosemicarbazides that consistently outperforms the analogous semicarbazide cyclizations. Various 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles have been prepared in good yields.
S. J. Dolman, F. Gosselin, P. D. O'Shea, I. W. Davies, J. Org. Chem., 2006, 71, 9548-9551.

N-Isocyaniminotriphenylphosphorane, aldehydes, and benzoic acids undergo a one-pot, three-component reaction under mild conditions to afford 2-aryl-5-hydroxyalkyl-1,3,4-oxadiazoles in good yields.
M. Adib, M. R. Kesheh, S. Ansari, H. R. Bijanzadeh, Synlett, 2009, 1575-1578.

Symmetric and unsymmetric 1,3,4-oxadiazoles were synthesized in situ from hydrazine hydrate and the corresponding 2-acyl-4,5-dichloropyridazin-3-ones as acylating agents in polyphosphoric acid (PPA) or BF₃·OEt₂ in excellent yields.
Y.-D. Park, J.-J. Kim, H.-A. Chung, D.-H. Kweon, S.-D. Cho, S.-G. Lee, Y.-J. Yoon, Synthesis, 2003, 560-564.

A simple and straightforward method for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO₂ as the C1 source requires no metal catalyst and only Cs₂CO₃ as the base. A good functional group tolerance is achieved.
O. Vechorkin, N. Hirt, X. Hu, Org. Lett., 2010, 12, 3567-3569.