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 |
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Authors: | V M Chernyshev A E Kosov E S Gladkov S V Shishkina V A Taranushich S M Desenko O V Shishkin |
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Institution: | (1) South-Russian State Technical University, 132 ul. Prosveshcheniya, 346428 Novocherkassk, Russian Federation;(2) State Scientific Institution “Institute for Single Crystals,”, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 61001 Kharkov, Ukraine |
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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.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 329–334, February, 2006. |
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Keywords: | thiosemicarbazide N-cyanoguanidine 3 5-diamino-1-thiocarbamoyl-1 2 4-triazole 3 5-diamino-1-thiazol-2-yl-1 2 4-triazoles α -halo ketones acylation hydrogenation X-ray diffraction study |
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