Advertisement

Russian Journal of Organic Chemistry

, Volume 55, Issue 5, pp 602–607 | Cite as

Synthesis of Methyl 4-Aryl-4-oxo-2-{4-[(1,3-thiazol-2-yl)-sulfamoyl]phenylamino}but-2-enoates and Their Reactions with Ninhydrin

  • V. L. GeinEmail author
  • O. V. Bobrovskaya
  • A. A. Russkikh
  • M. V. Dmitriev
  • A. N. Yankin
Article
  • 17 Downloads

Abstract

The reaction of methyl aroylpyruvates with 2-(4-aminobenzenesulfonamido)thiazole (norsulfazole) in acetic acid-ethanol (1: 1) afforded methyl (2Z)-4-aryl-4-oxo-2-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl-amino} but-2-enoates which reacted with ninhydrin in glacial acetic acid to give 4-aroyl-3-{4-[(1,3-thiazol-2-yl)-sulfamoyl]phenylamino} spiro[2,5-dihydrofuran-5,2′-indane]-2,1′,3′-triones.

Keywords

methyl (2Z)-4-aryl-4-oxo-2-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenylamino} but-2-enoates 2-(4-aminobenzenesulfonamido)thiazole (norsulfazole) ninhydrin 4-aroyl-3-{4-[(1,3-thiazol-2-yl)sulfamoyl]-phe-nylamino} spiro[2,5-dihydrofuran-5,2′-indane]-2,1′,3′-triones, synthesis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

The studies were carried out using the equipment of the resource centers of the Science Park of St. Petersburg State University “Chemistry Educational Center,” “Chemical Analysis and Materials Research Center,” and “Magnetic Resonance Research Centre.”

References

  1. 1.
    Perevalov, S.G., Burgart, Ya, V., Saloutin, V.I., and Chupakhin, O.N., Russ. Chem. Rev., 2001, vol. 70, p. 921. doi 10.1070/RC2001v070n11ABEH000685CrossRefGoogle Scholar
  2. 2.
    Gein, V.L., Bobrovskaya, O.V., Kovtonogova, I.V., Belonogova, V.D., Danilov, Yu.L., Nasakin, O.E., and Kazantseva, M.I., Russ. J. Org. Chem., 2016, vol. 52, p. 1764. doi  https://doi.org/10.1134/S1070428016120083 Google Scholar
  3. 3.
    Gein, V.L., Bobrovskaya, O.V., Kovtonogova, I.V., Seliverstov, G.V., Russkih, A.A., Belonogova, V.D., Anisimova, A.G., and Yagontseva, T.A., Butlerov Commun., 2016, vol. 48, p. 26. doi jbc-02/16-48-12-26Google Scholar
  4. 5.
    Kozlov, A.P., Varkentin, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1989, vol. 25, p. 1991.Google Scholar
  5. 6.
    Andreichikov, Yu.S., Kozlov, A.P., Tendryakova, S.P., and Nalimova, Yu.A., Zh. Org. Khim., 1977, vol. 13, p. 2559.Google Scholar
  6. 7.
    Kozlov, A.P., Doctoral Sci. (Chem.) Dissertation, Saratov, 1996.Google Scholar
  7. 8.
    Andreichikov, Yu.S., Kozlov, A.P., Tokmakova, T.N., and Tendryakova, S.P., Zh. Org. Khim., 1978, vol. 14, p. 163.Google Scholar
  8. 9.
    Dubovtsev, A.Yu., Candidate Sci. (Chem.) Dissertation, Perm, 2017.Google Scholar
  9. 10.
    Mahdavinia, G.H., Mohammadizadeh, M.R., Ariapour, N., and Alborz, M., Tetrahedron Lett., 2014, vol. 55, p. 1967. doi  https://doi.org/10.1016/j.tetlet.2013.10.156 CrossRefGoogle Scholar
  10. 11.
    Han, Y., Wu, Q., Sun, J., and Yan, C.-G., Tetrahedron, 2012, vol. 68, p. 8539. doi  https://doi.org/10.1016/j.tet.2012.08.030 CrossRefGoogle Scholar
  11. 12.
    Barbier, V., Couty, F., and David, O.R.P., Tetrahedron, 2016, vol. 72, p. 5646. doi  https://doi.org/10.1016/j.tet.2016.07.072 CrossRefGoogle Scholar
  12. 13.
    Kramer, H.J., Kessler, D., Hipler, U.C., Irlinger, B., Hort, W., Bodeker, R.H., Steglich, W., and Mayser, P., Chembiochem., 2005, vol. 6, p. 2290. doi  https://doi.org/10.1002/cbic.200500163 CrossRefPubMedGoogle Scholar
  13. 14.
    Malassezia and the Skin. Science and Clinical Practice, Boekhout, T., Guého-Kellermann, E., Mayser, P., and Velegraki, A., Eds., Berlin, Heidelberg: Springer-Verlag, 2010.Google Scholar
  14. 15.
    VI. Human and Animal Relationships, 2nd Ed., Brakhage, A.A. and Fzipfel, P., Eds., Berlin, Heidelberg: Springer-Verlag, 2008.Google Scholar
  15. 16.
    Gein, V.L., Gein, L.F., Sheptukha, M.A., and Voronina, E.V., Pharm. Chem. J., 2005, vol. 39, p. 537. doi  https://doi.org/10.1007/s11094-006-0016-8 CrossRefGoogle Scholar
  16. 17.
    Gein, L.F., Doctoral Sci. (Chem.) Dissertation, Perm, 2009.Google Scholar
  17. 18.
    Gein, V.L., Gein, L.F., Kuznetsova, E.D., and Aliev, Z.G., Chem. Heterocycl. Compd., 2005, vol. 41, p. 255. doi  https://doi.org/10.1007/s10593-005-0137-0 CrossRefGoogle Scholar
  18. 19.
    Gein, V.L., Bobrovskaya, O.V., and Dmitriev, M.V., Russ. J. Org. Chem., 2017, vol. 53, p. 898. doi  https://doi.org/10.1134/S1070428017060148 CrossRefGoogle Scholar
  19. 20.
    CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET).Google Scholar
  20. 21.
    Sheldrick, G.M., Acta Cryst., 2008, vol. A64, p. 112. doi  https://doi.org/10.1107/S0108767307043930 CrossRefGoogle Scholar
  21. 22.
    Sheldrick, G.M. Acta Cryst., 2015, vol. C71, p. 3. doi  https://doi.org/10.1107/S2053229614024218 Google Scholar
  22. 23.
    Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. doi  https://doi.org/10.1107/S0021889808042726 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • V. L. Gein
    • 1
    Email author
  • O. V. Bobrovskaya
    • 1
  • A. A. Russkikh
    • 1
  • M. V. Dmitriev
    • 2
  • A. N. Yankin
    • 3
  1. 1.Perm State Pharmaceutical AcademyPermRussia
  2. 2.Perm State National Research UniversityPermRussia
  3. 3.St. Petersburg State UniversitySt. PetersburgRussia

Personalised recommendations