Abstract
The reaction of thiosemicarbazide with N-cyanoguanidine in an acidic medium afforded 3,5-diamino-1-thiocarbamoyl-1,2,4-triazole, whose condensation with α-halo ketones gave 3,5-diamino-1-thiazol-2-yl-1,2,4-triazoles 7a–d. The latter were also prepared by the independent synthesis from 2-hydrazinothiazoles and N-cyanoguanidine. Acylation of compounds 7a,d under mild conditions and their condensation with aldehydes occur at the C(3′)NH2group. The structure of aroyl derivative 11c was established by X-ray diffraction. Acylation of diaminothiazolyltriazole 7a in boiling Ac2O afforded 3,5-diacetylamino-1-(4-phenylthiazol-2-yl)-1,2,4-triazole. Hydrogenation of arylidene derivatives 14b,c and aroyl derivative 11c gave the corresponding benzylaminotriazoles 15a,b.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 329–334, February, 2006.
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Chernyshev, V.M., Kosov, A.E., Gladkov, E.S. et al. Reaction of thiosemicarbazide with n-cyanoguanidine: synthesis of 3,5-diamino-1-thiocarbamoyl-and 3,5-diamino-1-thiazol-2-yl-1,2,4-triazoles. Russ Chem Bull 55, 338–344 (2006). https://doi.org/10.1007/s11172-006-0257-4
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DOI: https://doi.org/10.1007/s11172-006-0257-4