Abstract
The reaction of ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo[5,1-c][1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS.
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Dotsenko, V.V., Sventukh, D.V., and Krivokolysko, S.G., Chem. Heterocycl. Compd., 2012, vol. 48, no. 9, p. 1397. doi 10.1007/s10593-012-1149-1
Fesenko, A.A. and Shutalev, A.D., Tetrahedron, 2011, vol. 67, no. 36, p. 6876. doi 10.1016/j.tet.2011.06.089
Fesenko, A.A., Trafimova, L.A., and Shutalev, A.D., Org. Biomol. Chem., 2012, vol. 10, no. 2, p. 447. doi 10.1039/C1OB06284K
Baggs, M.E.M. and Gregory, B., Can. J. Chem., 1980, vol. 58, p. 794. doi 10.1139/v80-124
Bullock, E., Gregory, B., and Thomas, M.T., Can. J. Chem., 1977, vol. 55, p. 693. doi 10.1139/v77-098
Fesenko, A.A. and Shutalev, A.D., Chem. Heterocycl. Compd., 2013, vol. 49, no. 6, p. 827. doi 10.1007/s10593-013-1318-x
Ashby, J. and Griffiths, D.J., J. Chem. Soc., Perkin Trans. 1, 1975, p. 657. doi 10.1039/P19750000657
Bullock, E., Garter, R.A., Cochrane, R., Gregory, B., and Shields, V.S., Can. J. Chem., 1977, vol. 55, no. 5, p. 895. doi 10.1139/v77-124
Claremon, D.A. and Rosenthal, S.A., Synthesis, 1986, no. 8, p. 664. doi 10.1055/s-1986-31740
Ashby, J. and Griffiths, D., J. Chem. Sos., Chem. Commun., 1974, p. 607. doi 10.1039/C39740000607
Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed., San Diego: Academic, 1999, vol.74.
Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, no. 12, p. S1–S19. doi 10.1039/P298700000S1
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 301.
Ledenyova, I.V., Didenko, V.V., Shestakov, A.S., and Shikhaliev, Kh.S., Chem. Heterocycl. Compd., 2010, vol. 46, no. 6, p. 770. doi 10.1007/s10593-010-0584-0
Suchy, M., Elmehriki, A.A.H., and Hudson, R.H.E., Org. Lett., 2001, vol. 13, no. 15, p. 3952. doi 10.1021/ol201475j
Tietze, L.F., Brasche, G., and Gericke, K.M., Domino Reactions in Organic Synthesis, Weinheim: Wiley-VCH, 2006.
Yang, D. and Jeon, H.B., Bull. Korean Chem. Soc., 2010, vol. 31, no. 5, p. 1424. doi 10.5012/bkcs.2010.31.5.1424
Barlett, R.K. and Humphrey, I.R., J. Chem. Soc. C, 1967, p. 1664. doi 10.1039/J39670001664
Zhang, Q. and Chen, C., J. Saudi Chem. Soc., 2016, vol. 20, no. 1, p. 114. doi 10.1016/j.jscs.2014.09.006
Kislina, I.S., Librovich, N.V., Maiorov, V.D., Tarakanova, E.G., and Yukhnevich, G.V., Kinet. Catal., 2002, vol. 43, no. 5, p. 671. doi 10.1023/A:1020699928816
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930
Gilligan, P.J., Baldauf, C., Cocuzza, A., Chidester, D., Zaczek, R., Fitzgerald, L.W., McElroy, J., Smith, M.A., Shen, H.-S.L., Saye, J.A., Christ, D., Trainor, G., Robertson, D.W., and Hartig, P., Bioorg. Med. Chem., 2000, vol. 8, p. 181. doi 10.1016/S0968-0896(99)00271-0
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Original Russian Text © I.V. Ledenyova, A.V. Falaleev, Kh.S. Shikhaliev, E.A. Ryzhkova, F.I. Zubkov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 1, pp. 77–83.
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Ledenyova, I.V., Falaleev, A.V., Shikhaliev, K.S. et al. Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism. Russ J Gen Chem 88, 73–79 (2018). https://doi.org/10.1134/S1070363218010115
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DOI: https://doi.org/10.1134/S1070363218010115