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Reaction of 3-Aryl-2-Cyanoprop-2-ene- Thioamides With Bromonitromethane: A new Method for the Synthesis of Functionalized 1,2,4-Thiadiazoles

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 3-aryl-2-cyanoprop-2-enethioamides with bromonitromethane leads to the products of oxidative dimerization, (2Е,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis(3-arylacrylonitriles). Their structure was confirmed by the counter synthesis through the oxidation of 3-aryl-2-cyanoprop-2-ene-thioamides by DMSO–HCl system.

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References

  1. J.-M. Zhang, Synlett, 1692 (2009).

  2. B. R. Fishwick, D. K. Rowles, and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 835 (1983).

  3. N. Ono, in: H. Feuer (editor), The Nitro Group in Organic Synthesis, Wiley-VCH, New York (2001), p. 150.

    Chapter  Google Scholar 

  4. B. R. Fishwick, D. K. Rowles, and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 834 (1983).

  5. B. R. Fishwick, D. K. Rowles, and C. J. M. Stirling, J. Chem. Soc., Perkin Trans. 1, 1171 (1986).

  6. K. Gewald and U. Hain, Monatsh. Chem., 123, 455 (1992).

    Article  CAS  Google Scholar 

  7. D. Thomae, J. C. Rodriguez Dominguez, G. Kirsch, and P. Seck, Tetrahedron, 64, 3232 (2008).

    Article  CAS  Google Scholar 

  8. J. Liebscher, B. Abegaz, and A. Areda, J. Prakt. Chemie, 325, 168 (1983).

    Article  CAS  Google Scholar 

  9. D. Thomae, E. Perspicace, Z. Xu, D. Henryon, S. Schneider, S. Hesse, G. Kirsch, and P. Seck, Tetrahedron, 65, 2982 (2009).

    Article  CAS  Google Scholar 

  10. R. Niess and H. Eilingsfeld, DE Pat. Appl. 2241717.

  11. R. P. Alexander, J. M. Davis, M. C. Hutchings, V. E. Laing, and G. P. Trevitt, WO Pat. Appl. 2005042540.

  12. G. V. Klokol, Yu. A. Sharanin, V. K. Promonenkov, V. P. Litvinov, and V. S. Bogdanov, Zh. Org. Khim., 25, 1788 (1989). [Russ. J. Org. Chem., 25, 1616 (1989).]

  13. F. Guerrera, M. A. Siracusa, B. Tornetta, P. Agozzino, L. LaMartina, and E. Bousquet, J. Heterocycl. Chem., 21, 587 (1984).

    Article  CAS  Google Scholar 

  14. J. E. Campbell, P. Jones, and M. C. Hewitt, US Pat. Appl. 2012178748.

  15. V. P. Kislyi, V. N. Nesterov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 1150 (1999). [Russ. Chem. Bull., Int. Ed., 48, 1139 (1999).]

  16. V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 134 (2012). [Russ. Chem. Bull., Int. Ed., 61, 136 (2012).]

  17. V. V. Dotsenko, S. G. Krivokolysko, V. V. Polovinko, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 328 (2012). [Chem. Heterocycl. Compd., 48, 309 (2012).]

  18. V. V. Dotsenko, K. A. Frolov, and S. G. Krivokolysko, Khim. Geterotsikl. Soedin., 689 (2012). [Chem. Heterocycl. Compd., 48, 642 (2012).]

  19. K. A. Frolov, V. V. Dotsenko, and S. G. Krivokolysko, Khim. Geterotsikl. Soedin., 1668 (2012). [Chem. Heterocycl. Compd., 48, 1555 (2012).]

  20. V. V. Dotsenko and S. G. Krivokolysko, Khim. Geterotsikl. Soedin., 1680 (2012). [Chem. Heterocycl. Compd., 48, 1568 (2012).]

  21. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, and A. N. Chernega, Khim. Geterotsikl. Soedin., 716 (2007). [Chem. Heterocycl. Compd., 43, 599 (2007).]

  22. V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Monatsh. Chem., 139, 271 (2008).

    Article  CAS  Google Scholar 

  23. V. P. Litvinov, V. V. Dotsenko, and S. G. Krivokolysko, Izv. Akad. Nauk, Ser. Khim., 847 (2005). [Russ. Chem. Bull., Int. Ed., 54, 864 (2005).]

  24. R. N. Hurd and G. DeLaMater, Chem. Rev., 61, 45 (1961).

    Article  CAS  Google Scholar 

  25. L. Forlani and C. Boga, J. Chem. Soc., Perkin Trans. 2, 768 (2002)

    Article  Google Scholar 

  26. L. Forlani, A. Lugli, C. Boga, A. Bonamartini Corradi, and P. Sgarabotto, J. Heterocycl. Chem., 37, 63 (2000).

    Article  CAS  Google Scholar 

  27. Y. Takikawa, K. Shimada, K. Sato, S. Sato, and S. Takizawa, Bull. Chem. Soc. Jpn., 58, 995 (1985).

    Article  CAS  Google Scholar 

  28. V. V. Dotsenko and S. G. Krivokolysko, Khim. Geterotsikl. Soedin., 682 (2013). [Chem. Heterocycl. Compd., 48, 642 (2013).]

  29. J. Liebscher and H. Hartmann, Liebigs Ann. Chem., 1005 (1977).

  30. J. S. A. Brunskill, A. De, and D. F. Ewing, J. Chem. Soc., Perkin Trans. 1, 629 (1978).

  31. V. J. Grinsteins and L. A. Sherin', Izv. Akad. Nauk Latv. SSR, Ser. Khim., 469 (1963); Chem. Abstr., 60, 5392b (1964).

  32. V. D. Dyachenko, S. G. Krivokolysko, and V. P. Litvinov, Mendeleev Commun., 8, 23 (1998).

    Article  Google Scholar 

  33. M. A. Aboutabl, M. A. Abdel Aziz, A. A. Magd El Din, H. A. Elwy, and H. M. Fahmy, Monatsh. Chem., 122, 765 (1991).

    Article  CAS  Google Scholar 

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Correspondence to V. V. Dotsenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 607-613, April, 2014.

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Dotsenko, V.V., Krivokolysko, S.G. Reaction of 3-Aryl-2-Cyanoprop-2-ene- Thioamides With Bromonitromethane: A new Method for the Synthesis of Functionalized 1,2,4-Thiadiazoles. Chem Heterocycl Comp 50, 557–563 (2014). https://doi.org/10.1007/s10593-014-1507-2

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