Synthesis and heterocyclization reaction of tribenzylbenzene sulfonylimino chloride with various polarophiles

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A new method has been developed for the preparation of multifunctional pyrazoles by the reaction of 1,3-dipolar addition of tribenzylsulfonyliminochloride to polarophiles. This imine was obtained by reacting tribenzylamine with N -chlorobenzenesulfamide (chloramine-B). Regardless of the structure and composition of polarophiles, the cyclization reaction takes place in the presence of alkali for 6-8 h of boiling, which proves the activation of the methylene groups of tribenzylamine with the help of an electron-withdrawing sulfamide group.

作者简介

A. Makhmudova

Institute of Chemistry of Additives named after A.Kuliyev of the National Academy of Sciences of Azerbaijan

Email: iradam@rambler.ru

参考

  1. Ye X.M., Konradi A.W., Sun M., Yuan Sh., Aubele D.L., Dappen M., Dressen D., Garofalo A.W., Jagodzinski J.J., Latimer L., Probst G.D., Sham H.L., Wone D., Xu Y.-z., Ness D., Brigham E., Kwong G.T., Willtis C., Tonn G., Goldbach E., Quinn K.P., Zhang H.H., Sauer J.-M., Bova M., Basi G.S. Bioorg. Med. Chem. Lett. 2013, 23, 996-1000. doi: 10.1016/j.bmcl.2012.12.039
  2. Lundy K.M., Cheng H., Sakya S.M., Li J., Minich M.L., Uchida Ch. Пат. US6531492B1 (2000). США.
  3. Soliman R., Faid-Allah H.M., El Sadany S.K. J. Pharm. Sci. 1987, 76, 626-632. doi: 10.1002/jps.2600760808
  4. Talley J.J., Penning T.D., Collins P.W., Rogier D.J. Jr., Malecha J.W., Miyashiro J.M., Bertenshaw S.R., Khanna I.K., Graneto M.J., Rogers R.S., Carter J.S., Docter S.H., Stella S.Yu. Пат. US6586603B1 (2002). США.
  5. Talley J.J., Penning T.D., Collins P.W., Rogier D.J. Jr., Malecha J.W., Miyashiro J.M., Bertenshaw S.R., Khanna I.K., Graneto M.J., Rogers R.S., Carter J.S., Docter S.H., Stella S.Yu. Пат. US6492411B1 (2002). США.
  6. Baxendale I.R., Ley S.V., Martinelli M. Tetrahedron. 2005, 61, 5323-5349. doi: 10.1016/j.tet.2005.03.062
  7. Hamad A.-S.S., Hashem A.I. J. Heterocycl. Chem. 2002, 33, 1325-1328. doi: 10.1002/jhet.5570390634
  8. Lee W.-C.C., Shen Y., Gutierrez D.A., Li J.J. Org. Lett. 2016, 18, 2660-2663. doi: 10.1021/acs.orglett.6b01105
  9. Omietanski G.M., Sisler H.H. J. Am. Chem. Soc. 1956, 78, 1211-1213. doi: 10.1021/ja01587a033
  10. Killer R.N., Smith P.A.S. J. Am. Chem. Soc. 1946, 68, 899-902. doi: 10.1021/ja01209a060
  11. Tamura Y., Minamikawa J., Miki Y., Matsugashita S., Ikeda M. Tetrahedron Lett. 1972, 13, 4133-4135. doi: 10.1016/S0040-4039(01)94256-X
  12. Мамедов С.А., Фарзалиев В.М., Шахгельдиева Л.М., Ладохина Н.П., Фатализаде Ф.А. Азерб. хим. ж. 2007, 3, 100-103.
  13. Mamedov S.A., Farzaliev V.M., Shakhgeldieva L.M., Ladokhina N.P., Fatalizade F.A. Azerbaijan Chem. J. 2007, 3, 100-103.
  14. Rovnyak G., Shu V., Schwartz J. J. Heterocycl. Chem. 1981, 18, 327-331. doi: 10.1002/jhet.5570180219
  15. Tamura Y., Sumida Y., Miki S., Ikeda M. J. Chem. Soc., Perkin. Trans. 1. 1975, 406-409. doi: 10.1039/P19750000406
  16. Харанеко А.О., Харанеко О.И. ЖОрХ. 2019, 55, 341-346.
  17. Kharaneko A.O., Kharaneko O.I. Russ. J. Org. Chem. 2019, 55, 291-295. doi: 10.1134/S1070428019030023
  18. Игнатович Ж.В., Ермолинская А.Л., Ольховик В.К., Матвеенко Ю.В., Королева Е.В. ЖОрХ. 2019, 55, 583-590.
  19. Ignatovich Zh.V., Ermolinskaya A.L., Ol'khovik V.K., Matveenko Yu.V., Koroleva E.V. Russ. J. Org. Chem. 2019, 55, 487-492. doi: 10.1134/S1070428019040110
  20. Никонова В.С., Калиев А.Р., Бородина Т.Н., Смирнов В.И., Розенцвейг И.Б., Корчевин Н.А. ЖОрХ. 2019, 55, 1926-1932.
  21. Nikonova V.S., Kaliev A.R., Borodina T.N., Smirnov V.I., Rosenzveig I.B., Korchevin N.A. Russ. J. Org. Chem. 2019, 55, 1912-1917. doi: 10.1134/S1070428019120170
  22. Мамедов С.А., Шахгельдиева Л.М., Мамедова С.И., Ладохина Н.П., Гусейнов И.Ш. ЖОрХ. 2012, 46, 1385-1386.
  23. Mamedov S.A., Shakhgel'dieva L.M., Mamedova S.I., Ladokhina N.P., Guseinov I.Sh. Russ. J. Org. Chem. 2012, 46, 1382-1383. doi: 10.1134/S1070428012100223
  24. Mamedova G., Mahmudova A., Mamedov S., Erden Y., Taslimi P., Tüzün B., Tas R., Farzaliyev V., Sujayev A., Alwasel S.H., Gulçin I. Bioorg. Chem. 2019, 93, 103313. doi: 10.1016/j.bioorg.2019.103313

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