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Technical University of Crete
Technical University of Crete
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| URI: | http://purl.tuc.gr/dl/dias/C1D7A97B-8880-49B4-AC9E-5A56716EB77C | ||
| Year | 2013 | ||
| Type of Item | Peer-Reviewed Journal Publication | ||
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| Bibliographic Citation | T. Zarganes-Tzitzikas, C. G. Neochoritis, J. Stephanidou-Stephanatou, C. A. Tsoleridis, G. Buth, and G. E. Kostakis, "Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazoles", Tetrahedron, vol. 69, no. 24, pp. 5008-5015, Jun. 2013. doi:10.1016/j.tet.2013.03.096 https://doi.org/10.1016/j.tet.2013.03.096 | ||
| Appears in Collections |
Upon reaction of 4,5-disubstituted-N-arylaminoimidazole-2-thiones with isocyanides in the presence of azodicarboxylates (1.2 equiv) at rt, the imidazo[2,1-b][1,3,4]thiadiazoles were formed as the only reaction products in very good yields, whereas by using higher reaction temperatures, along with the imidazo[2,1-b][1,3,4]thiadiazoles, the three component reaction products, namely thiadiazoles, were also isolated, their formation being dependent on the 5-thione substituent. The thiadiazoles became the only reaction products, formed in very good yield by using 2 equiv of azodicarboxylates. The sodium cyanoborohydride and sodium borohydride reductions to thiadiazoles 11, and 12 were also studied. Plausible mechanistic schemes for the formation of the thiadiazoles are proposed.
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