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4-Aryl-3-(methanesulfonyl)pyrazolo[5,1-c][1,2,4]triazines and their transformations

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Abstract

Coupling of 3-alkyl-4-aryl-1H-pyrazole-5-diazonium chlorides with methylene-active methyl phenacyl sulfones afforded new pyrazolo[5,1-c][1,2,4]triazine derivatives via cyclization of the corresponding intermediate 1-aryl-2-(hetarylhydrazinylidene)-2-(methanesulfonyl)ethanones. The reactivity of the methanesulfonyl group on C3 of pyrazolo[5,1-c][1,2,4]triazines toward some nucleophiles was studied.

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References

  1. Tozkoparan, B., Kupeli, E., and Yesilada, M., Bioorg. Med. Chem., 2007, vol. 15, p. 1808.

    Article  CAS  Google Scholar 

  2. Shaaban, O.G., Rizk, O.H., Bayad, A.E., and El-Ashmawy, I.M., Open Med. Chem. J., 2013, vol. 7, p. 49.

    Article  CAS  Google Scholar 

  3. Kudryavtsev, K.V., Bentley, M.L., and McCafferty, D.G., Bioorg. Med. Chem., 2009, vol. 17, no. 7, p. 2886.

    Article  CAS  Google Scholar 

  4. Guruswamy, B., Arul, R.K., Chaitanya, M.V., and Darsi, S.S.P.K., Eur. J. Chem., 2013, vol. 4, no. 4, p. 329.

    Article  CAS  Google Scholar 

  5. Cohen, A., Crozet, M.D., Rathelot, P., Azas, N., and Vanelle, P., Molecules, 2013, vol. 18, p. 97.

    Article  CAS  Google Scholar 

  6. Shagufta, I.A., Int. J. Pharm. Pharm. Sci., 2015, vol. 7, no. 3, p. 21.

    Google Scholar 

  7. Hong, Y.-S., Kim, H.-M., Park, Y.-T., and Kim, H.-S., Bull. Korean Chem. Soc., 2000, vol. 21, no. 1, p. 133.

    CAS  Google Scholar 

  8. Xu, W., He, J., He, M., Han, F., Chen, X., Pan, Zh., Wang, J., and Tong, M., Molecules, 2011, vol. 16, p. 9129.

    Article  CAS  Google Scholar 

  9. Oishi, E., Yamada, A., Hayashi, E., and Higashino, T., Chem. Pharm. Bull., 1987, vol. 35, no. 2, p. 514.

    Article  CAS  Google Scholar 

  10. Hassan, N.M., Fahmi, A.A., Abd-Elmageid, F.F., and Abdelhamid, A.O., J. Chin. Chem. Soc., 1996, vol. 43, p. 493.

    Article  CAS  Google Scholar 

  11. Saraiva, M.T., Costa, G.P., Seus, N., Schumacher, R.F., Márcio, G.P., Paixão, W., Luque, R., and Alves, D., Org. Lett., 2015, vol. 17, p. 6206.

    Article  CAS  Google Scholar 

  12. Rusinov, V.L., Ulomskii, E.N., Chupakhin, O.N., and Charushin, V.N., Russ. Chem. Bull., Int. Ed., 2008, vol. 57, no. 5, p. 985.

    Article  CAS  Google Scholar 

  13. Anwar, H.F. and Elnagdi, M.H., Arkivoc, 2009, part (i), p. 198.

    Google Scholar 

  14. Ledenyova, I.V., Didenko, V.V., and Shikhalie., Kh.S., Chem. Heterocycl. Compd., 2014, vol. 50, p. 1214.

    Article  CAS  Google Scholar 

  15. Ledenyova, I.V., Didenko, V.V., Shestakov, A.S., and Shikhalie., Kh.S., J. Heterocycl. Chem., 2013, vol. 50, p. 573.

    Article  CAS  Google Scholar 

  16. Ledenyova, I.V., Didenko, V.V., Dotsenko, V.V., and Shikhalie., Kh.S., Tetrahedron Lett., 2014, vol. 55, p. 1239.

    Article  CAS  Google Scholar 

  17. Ledenyova, I.V., Gracheva, A.A., and Shikhalie., Kh.S., Chem. Heterocycl. Compd., 2015, vol. 51, p. 734.

    Article  CAS  Google Scholar 

  18. Charushin, V.N., Alexeev, S.G., Chupakhin, O.N., and van der Plas, H.C., Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed., New York: Academic, 1989, vol. 46, p. 73.

    Article  CAS  Google Scholar 

  19. Taylor, E.C. and Macor, J.E., Tetrahedron Lett., 1986, vol. 27, p. 431.

    Article  CAS  Google Scholar 

  20. Radel, R.J., Atwood, J.L., and Paudler, W.W., J. Org. Chem., 1978, vol. 43, p. 2514.

    Article  CAS  Google Scholar 

  21. Kozhevnikov, D.N., Kovalev, I.S., Rusinov, V.L., and Chupakhin, O.N., Chem. Heterocycl. Compd., 2001, vol. 37, p. 1136.

    Article  CAS  Google Scholar 

  22. Kozhevnikov, D.N., Kozhevnikov, V.N., Kovalev, I.S., Rusinov, V.L., Chupakhin, O.N., and Aleksandrov, G.G., Russ. J. Org. Chem., 2002, vol. 38, p. 744.

    Article  CAS  Google Scholar 

  23. 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.

    Article  CAS  Google Scholar 

  24. Becker, H.D. and Russell, G.A., J. Org. Chem., 1963, vol. 28, p. 1896.

    Google Scholar 

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Correspondence to I. V. Ledenyova.

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Original Russian Text © I.V. Ledenyova, P.A. Kartavtsev, Kh.S. Shikhaliev, A.Yu. Egorova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1328–1333.

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Ledenyova, I.V., Kartavtsev, P.A., Shikhaliev, K.S. et al. 4-Aryl-3-(methanesulfonyl)pyrazolo[5,1-c][1,2,4]triazines and their transformations. Russ J Org Chem 52, 1316–1321 (2016). https://doi.org/10.1134/S1070428016090116

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  • DOI: https://doi.org/10.1134/S1070428016090116

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