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Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 689–699 | Cite as

A Convenient Approach to 2-Aminobenzo[b]chalcogenophenes Based on Copper-Catalyzed Transformation of 4-(2-Bromophenyl)-1,2,3-chalcogenodiazoles in the Presence of a Base and Amines

  • E. A. Popova
  • A. G. Lyapunova
  • M. L. Petrov
  • T. L. Panikorovskii
  • D. A. Androsov
Article
  • 5 Downloads

Abstract

The reactions of 4-(2-bromophenyl)-1,2,3-thia-and -selenadiazoles with amines in the presence of potassium carbonate and copper(I) iodide afforded 2-aminobenzo[b]chalcogenophenes. The corresponding thiaand selenamides, prepared by interaction of 4-(2-bromophenyl)-1,2,3-thia- and -selenadiazoles with amines in the absence of copper salt, were transformed into 2-aminobenzo[b]chalcogenophenes by the action of potassium carbonate and copper(I) iodide in DMF in different yields.

Keywords

benzo[b]thiophene benzo[b]selenophene 1,2,3-thiadiazole 1,2,3-selenadiazole copper-catalyzed cyclization 

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Notes

Acknowledgments

This work was financially supported by the Ministry of Education and Science of the Russian Federation within the framework of the state project (project no. 4.5554.2017/8.9) using the equipment of the X-ray Diffraction Center of St. Petersburg State University and the Engineering Center of the St. Petersburg State Institute of Technology (Technical University).

References

  1. 1.
    Chonan, T., Wakasusugi, D., Yamamoto, D., Yashiro, M., Oi, T., Tanaka, H., Ohoka-Sugita, A., Io, F., Koretsune, H., and Hiratate, A., Bioorg. Med. Chem., 2011, vol. 19, p. 1580. doi 10.1016/j.bmc.2011.01.041CrossRefGoogle Scholar
  2. 2.
    Kamata, M., Yamashita, T., Kina, A., Funata, M., Mizukami, A., Sasaki, M., Tani, A., Funami, M., Amano, N., and Fukatsu, K., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 3643. doi 10.1016/j.bmcl.2012.04.047CrossRefGoogle Scholar
  3. 3.
    Romagnoli, R., Baraldi, P.G., Lopez-Cara, C., Preti, D., Aghazadeh Tabrizi, M., Balzarini, J., Bassetto, M., Brancale, A., Fu, X.-H., Gao, Y., Li, J., Zhang, S.-Z., Hamel, E., Bortolozzi, R., Basso, G., and Viola, G., J. Med. Chem., 2013, vol. 56, p. 9296. doi 10.1021/jm4013938CrossRefGoogle Scholar
  4. 4.
    Romagnoli, R., Baraldi, P.G., Carrion, M.D., Cruz-Lopez, O., Tolomeo, M., Grimaudo, S., Cristina, A.D., Pipitone, M.R., Bal-zarini, J., and Brancale, A., Bioorg. Med. Chem., 2010, vol. 18, p. 5114. doi 10.1016/j.bmc.2010.05.068CrossRefGoogle Scholar
  5. 5.
    Romagnoli, R., Baraldi, P.G., Carrion, M.D., Cara, C.L., Preti, D., Fruttarolo, F., Pavani, M.G., Tabrizi, M.A., Tolomeo, M., Grimaudo, S., J. Med. Chem., 2007, vol. 50, p. 2273. doi 10.1021/jm070050fCrossRefGoogle Scholar
  6. 6.
    Grese, T.A., Cho, S., Finley, D.R., Godfrey, A.G., Jones, C.D., Lugar, C.W., Martin, M.J., Matsumoto, K., Pennington, L.D., and Winter, M.A., J. Med. Chem., 1997, vol. 40, p. 146. doi 10.1021/jm9606352CrossRefGoogle Scholar
  7. 7.
    Grese, T.A., Pennington, L.D., Sluka, J.P., Adrian, M.D., Cole, H.W., Fuson, T.R., Magee, D.E., Phillips, D.L., Rowley, E.R., and Shetler, P.K., J. Med. Chem., 1998, vol. 41, p. 1272. doi 10.1021/jm970688zCrossRefGoogle Scholar
  8. 8.
    Ebata, H., Miyazaki, E., Yamamoto, T., and Takimiya, K., Org. Lett., 2007, vol. 9, p. 4499. doi 10.1021/ol701815jCrossRefGoogle Scholar
  9. 9.
    Hari, D.P., Hering, T., and Konig, B., Org. Lett., 2012, vol. 14, p. 5334. doi 10.1021/ol302517nCrossRefGoogle Scholar
  10. 10.
    Mori, T., Nishimura, T., Yamamoto, T., Doi, I., Miyazaki, E., Osaka, I., and Takimiya, K., J. Am. Chem. Soc., 2013, vol. 135, p. 13900. doi 10.1021/ja406257uCrossRefGoogle Scholar
  11. 11.
    Ruzie, C., Karpinska, J., Kennedy, A.R., and Geerts, Y.H., J. Org. Chem., 2013, vol. 78, p. 7741. doi 10.1021/jo401134cCrossRefGoogle Scholar
  12. 12.
    Acharya, A., Kumar, S.V., Saraiah, B., and Ila, H., J. Org. Chem., 2015, vol. 80, no. 5, p. 2884. doi 10.1021/acs.joc.5b00032CrossRefGoogle Scholar
  13. 13.
    Kashiki, T., Shinamura, S., Kohara, M., Miyazaki, E., Takimiya, K., Ikeda, M., and Kuwabara, H., Org. Lett., 2009, vol. 11, p. 2473. doi 10.1021/ol900809wCrossRefGoogle Scholar
  14. 14.
    Rhoden, C.R.B. and Zeni, G., Org. Biomol. Chem., 2011, vol. 9, p. 1301. doi 10.1039/C0OB00557FCrossRefGoogle Scholar
  15. 15.
    Stacy, G., Wollner, T., and Villaescusa, F., J. Org. Chem., 1965, vol. 30, p. 4074. doi 10.1021/jo01023a021CrossRefGoogle Scholar
  16. 16.
    Del Amo, V., Dubbaka, S., Krasovskiy, A., and Knochel, P., Angew. Chem. Int. Ed., 2006, vol. 45, p. 7838. doi 10.1002/anie.200603089CrossRefGoogle Scholar
  17. 17.
    Hou, C., He, Q., and Yang, C., Org. Lett., 2014, vol. 16, p. 3040. doi 10.1021/ol502381eCrossRefGoogle Scholar
  18. 18.
    Grandclaudon, P. and Lablache-Combier, A., J. Org. Chem., 1978, vol. 43, p. 4379. doi 10.1021/jo00416a032CrossRefGoogle Scholar
  19. 19.
    Brower, K. and Amstutz, E., J. Org. Chem., 1954, vol. 19, p. 411. doi 10.1021/jo01368a019CrossRefGoogle Scholar
  20. 20.
    Ablenas, F., George, B., Maleki, M., Jain, R., Hopkinson, A., and Lee-Ruff, E., Can. J. Chem., 1987, vol. 65, p. 1800. doi 10.1139/v87-302CrossRefGoogle Scholar
  21. 21.
    Abramenko, P. and Zhiryakov, V., Chem. Heterocycl. Compd., 1977, p. 1194. doi 10.1007/BF00475943.Google Scholar
  22. 22.
    Deprets, S. and Kirsch, G., Eur. J. Org. Chem., 2000, p. 1353. doi 10.1002/1099-0690(200004)2000:7<1353::AID-EJOC1353>3.0.CO,2-AGoogle Scholar
  23. 23.
    L’abbe, G., Dekerk, J.-P., Martens, C., and Toppet, S., J. Org. Chem., 1980, vol. 45, p. 4366. doi 10.1021/jo01310a020CrossRefGoogle Scholar
  24. 24.
    Androsov, D.A., Solovyev, A.Y., Petrov, M.L., Butcher, R., and Jasinski, J., Tetrahedron, 2010, vol. 66, p. 2474. doi 10.1016/j.tet.2010. 01.069CrossRefGoogle Scholar
  25. 25.
    Lyapunova, A.G., Androsov, D.A., and Petrov, M.L., Tetrahedron Lett., 2013, vol. 54, p. 3427. doi 10.1016/j.tetlet.2013.04.077CrossRefGoogle Scholar
  26. 26.
    Androsov, D.A., Popova, E.A., Petrov, M.L., and Ponyaev, A.I., Russ. J. Gen. Chem., 2014, vol. 84, p. 2405. doi 10.1134/S1070363214120093CrossRefGoogle Scholar
  27. 27.
    Butler, R.N. and O’Donoqhue, D.A., J. Chem. Soc. Perkin Trans. 1, 1982, p. 1223. doi 10.1039/P19820001223Google Scholar
  28. 28.
    Caplin, A., J. Chem. Soc. Perkin Trans. 1, 1974, p. 30. doi 10.1039/P19740000030Google Scholar
  29. 29.
    Hurd, C.D. and Mori, R.I., J. Am. Chem. Soc., 1955, vol. 77, p. 5359. doi 10.1021/ja01625a047.CrossRefGoogle Scholar
  30. 30.
    Cheung, E., Pennington, L., Bartbergerb, M., and Staples, R., Acta Crystallogr. (C), 2014, vol. 70, p. 547. doi 10.1107/S2053229614009401Google Scholar
  31. 31.
    Dimmock, J., Sidhu, K., Tumber, S., Basran, S., Chen, M., Quali, J., Yang, J., Rozas, I., and Weaver, D., Eur. J. Med. Chem., 1995, vol. 30, p. 287. doi 10.1016/0223-5234(96)88237-7CrossRefGoogle Scholar
  32. 32.
    Lutz, R., Allison, R., Ashburn, G., Bailey, Ph., Clark, M., Codington, J., Deinet, A., Freek, J., Jordan, R., Leake, N., Martin, T., Nicodemus, K., Rowlett, R., Jr., Shearer, N., Jr., Smith, J., and Wilson, J., J. Org. Chem., 1947, vol. 12, p. 617. doi 10.1021/jo01169a001CrossRefGoogle Scholar
  33. 33.
    Hu, Y., Baudart, S., and Porco, J.A., Jr., J. Org. Chem., 1999, vol. 64, p. 1049. doi 10.1021/jo981874vCrossRefGoogle Scholar
  34. 34.
    King, J. and McMillan, F., J. Am. Chem. Soc., 1946, vol. 68, p. 2335. doi 10.1021/ja01215a058CrossRefGoogle Scholar
  35. 35.
    McDonald, S.L., Hendrick, C.E, and Wang, Q., Angew. Chem. Int. Ed., 2014, vol. 53, p. 1. doi 10.1002/anie.201311029CrossRefGoogle Scholar
  36. 36.
    Chippendale, K.E., Iddon, B., Suschitzky, H., and Taylor, D.S., J. Chem. Soc. Perkin Trans. 1, 1974, p. 1168. doi 10.1039/P19740001168Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • E. A. Popova
    • 1
  • A. G. Lyapunova
    • 2
  • M. L. Petrov
    • 1
  • T. L. Panikorovskii
    • 2
  • D. A. Androsov
    • 1
  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia
  2. 2.St. Petersburg State UniversitySt. PetersburgRussia

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