Skip to main content
Log in

Geminal acylnitrostyrenes in the reaction with ortho-aminothiophenol

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The synthesis of previously unknown 2,3- and 2,5-dihydro-1,5-benzothiazepines sontaining nitro group was performed by the easy sondensation of geminal acylnitrostyrenes with the o-aminothiophenol. The structure of the obtained sompounds was studied by physicochemical methods. By X-ray diffraction analysis the geometry and structural parameters of 4-methyl-3-nitro-2-phenyl-2,3-dihydro-1,5-benzothiazepine were determined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Orlov, V.D, Kolosov, M.A., Kotlyar, V.N. Marrugo Gonzalez, A.Kh., Sidorenko, D.Yu., Pushkarev, A.P., and Baraban, A.Yu., in Korshunovskie chteniya (Korshunov Readings), All-Russian Scientific and Practical Conf., Tol’yatti, 2008, p. 11.

  2. Shikhaliev Kh.E., Falaleev, A.V., and Kryl’skii, D.V., Izbrannye metody sinteza i modifikatsii geterocyclov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS Press, 2003, vol. 1, p. 450.

    Google Scholar 

  3. Desenko, S.M., Chebanov, V.A., Kolos, N.N., and Orlov, V.D., Izbrannye metody sinteza i modifikatsii geterocyclov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS Press, 2003, vol. 1, p. 140.

    Google Scholar 

  4. Desenko, S.M. and Orlov, V.D., Azageterotsikly na osnove aromaticheskikh nepredel’nykh ketonov (Aza-Heterocycles Based on Aromatic Unsaturated Ketones), Khar’kov: Folio, 1998.

    Google Scholar 

  5. Baichurin, R.I., Aboskalova, N.I., Berkova, G.A., and Berestovitskaya, V.M., Zh. Org. Khim., 2009, vol. 45, no. 8, p. 1196.

    Google Scholar 

  6. Remennikov, G.A., Khim. Geterotsikl. Soedinin., 1997, no. 12, p. 1587.

  7. Bakhareva, S.V., Aboskalova, N.I., and Berestovitskaya, V.M., Zh. Obshch. Khim., 2001, vol. 71, no. 9, p. 1577.

    Google Scholar 

  8. Aboskalova, N.I., Berestovitskaya, V.M., Bakhareva, S.V., and Fel’gendler, A.V., Khim. Geterotsikl. Soedin., 2002, no. 10, p. 1462.

  9. Berestovitskaya, V.M., Aboskalova, N.I., Ishmaeva, E.A., Bakhareva, S.V., Berkova, G.A., Vereshchagina Ya.A., Fel’gendler, A.V., and Fattakhova, G.R., Zh. Obsch. Khim., 2001, vol. 71, p. 2049.

    Google Scholar 

  10. Aboskalova, N.I., Smirnova, N.N., Kataeva, O.N., Baichurin, R.I., Fel’gendler, A.V., Berkova, G.A., and Berestovitskaya, V.M., Zh. Obsch. Khim., 2008, vol. 78, no. 9, p. 1478.

    Google Scholar 

  11. Fel’gendler, A.V., Aboskalova, N.I., and Berestovitskaya, V.M., Zh. Obsch. Khim., 2000, vol. 70, no. 7, p. 1158.

    Google Scholar 

  12. Cram, D.J. and Hammond, G.S., Organicheskaya khimiya (Organic Chemistry), Moscow: Mir, 1964, p. 288.

    Google Scholar 

  13. Morrison, R.T. and Boyd, R.N., Organicheskaya khimiya (Organic Chemistry), Moscow: Mir, 1974, p. 600.

    Google Scholar 

  14. Saikes, P., Reaction Mechanism in Organic Chemistry, Moscow: Khimiya, 2000, p. 107.

    Google Scholar 

  15. Khanna, M.S., Kumar, D., Garg, C.P., and Kapoor, R.P., Indian. J. Chem., Sect., B., 1995, vol. 34, no. 4, p. 333.

    Google Scholar 

  16. Orlov, V.D., Kolos, N.N., and Ruzhitskaya, N.N., Khim. Geterotsikl. Soedin., 1983, no. 12, p. 1638.

  17. Gupta, A.K., Singh, V.K., and Pant, U.C., Indian. J. Chem., Sect., B., 1983, vol. 22, no. 10, p. 1057.

    Google Scholar 

  18. Stephens, W. and Field, L., J. Org. Chem., 1959, vol. 24, no. 10, p. 1576.

    Article  CAS  Google Scholar 

  19. Khatik, G.L., Sharma, G., Kumar, R., and Chakraborty, A.K., Tetrahedron, 2007, vol. 63, no. 5, p. 1200.

    Article  CAS  Google Scholar 

  20. Sharma, G., Kumar, R., and Chakraborty, A.K., Tetrahedron Lett., 2008, vol. 49, no. 27, p. 4272.

    Article  CAS  Google Scholar 

  21. Wang, L., Zhang, P., Zhang, X., Zhang, Y., Li, Y., and Wang, Y., Eur. J. Med. Chem., 2009, vol. 44, no. 7, p. 2815.

    Article  CAS  Google Scholar 

  22. Li, W., Lan, J., Li, C., Cao, Y., Wang, H., Wang, L., Zhang, P., Wang, Y., and Li, Y., Acta Chimica Sinica (Huaxue Xuebao), 2009, vol. 67, no. 23, p. 2732.

    CAS  Google Scholar 

  23. Shirinyan, V.Z., Melkova, S.Yu., Belen’kii, L.I., Krayuskhin, M.M., Izv. Akad. Nauk, Ser. Khim., 2000, no. 11, p. 1887.

  24. Rajappa, S., Tetrahedron, 1999, vol. 55, no. 23, p. 7065.

    Article  CAS  Google Scholar 

  25. Kumar, R.R. and Perumal, S., Tetrahedron, 2007, vol. 63, no. 33, p. 7850.

    Article  CAS  Google Scholar 

  26. Parvez, M., Umbreen, S., Ansari, F.L., Acta Cryst., Sect., C., 2003, vol. 59, no. 6, p. o298.

    Article  Google Scholar 

  27. Sathunuru, R., Koh, B., Zhang, H., and Biehl, E., Heterocycles, 2005, vol. 65, no. 10, p. 2493.

    Article  CAS  Google Scholar 

  28. Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: RIA “Novaya Volna,” 2007, pp. 72, 433.

    Google Scholar 

  29. Registr lekarstvennykh sredstv Rossii. Encyclopediya lekarstv (Register of Drugs of Russa. Encyclopedia of Drugs), ┐RLS-2002,” 2002, vol. 9, pp. 298, 411.

  30. Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, no. 1, p. 112.

    Article  Google Scholar 

  31. Sokolov, N.A., Tishchenko, I.G., Karpitskaya, N.V., and Grinkevich, V.G., Vestn. Bel. Gos. Univ., 1978, no. 3, p. 29.

  32. Metody polucheniya khimicheskikh reagentov i preparatov (Methods of Obtaining Chemical Reagents and Preparations), Moscow: IREA, 1964, vol. 9, p. 26.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. M. Berestovitskaya.

Additional information

Original Russian Text © V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova, K.A. Lysenko, I.V. Anan’ev, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 6, pp. 970–977.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I. et al. Geminal acylnitrostyrenes in the reaction with ortho-aminothiophenol. Russ J Gen Chem 81, 1163–1170 (2011). https://doi.org/10.1134/S1070363211060156

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363211060156

Keywords

Navigation