Skip to main content
Log in

Synthesis of methyl 4-aryl-4-oxo-2-[(4-sulfamoylphenyl)amino]but-2-enoates and their reaction with ninhydrin

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

Abstract

The reaction of methyl 4-aryl-2,4-dioxobut-2-enoates with 4-aminobenzenesulfonamide in acetic acid–ethanol (1: 1) afforded methyl (2Z)-4-aryl-4-oxo-2-(4-sulfamoylanilino)but-2-enoates which reacted with ninhydrin in glacial acetic acid to give 3-aroyl-4-(4-sulfamoylanilino]-5H-spiro[furan-2,2′-indene]-1′,3′,5-triones.

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. 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, no. 12, p. 1764.

    Article  Google Scholar 

  2. Gein, V.L., Bobrovskaya, O.V., Kovtonogova, I.V., Seliverstov, G.V., Russkikh, A.A., Belonogova, V.D., Anisimova, A.G., and Yagontseva, T.A., Butlerov Commun., 2016, vol. 48, no. 12, p. 26. roi jbc-02/16-48-12-26

    Google Scholar 

  3. Kozlov, A.P., Varkentin, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1984, vol. 20, no. 10, p. 2198.

    CAS  Google Scholar 

  4. Kozlov, A.P., Varkentin, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1989, vol. 25, no. 9, p. 1991.

    CAS  Google Scholar 

  5. Andreichikov, Yu.S., Kozlov, A.P., Tendryakova, S.P., and Nalimova, Yu.A., Zh. Org. Khim., 1977, vol. 13, no. 12, p. 2559.

    CAS  Google Scholar 

  6. Kozlov, A.P., Doctoral (Chem.) Dissertation, Saratov, 1996.

  7. Andreichikov, Yu.S., Kozlov, A.P., Tokmakova, T.N., and Tendryakova, S.P., Zh. Org. Khim., 1978, vol. 14, no. 1, p. 163.

    CAS  Google Scholar 

  8. Mahdavinia, G.H., Mohammadizadeh, M.R., Ariapour, N., and Alborz, M., Tetrahedron Lett., 2014, vol. 55, p. 1967.

    Article  CAS  Google Scholar 

  9. Han, Y., Wu, Q., Sun, J., and Yan, C.-G., Tetrahedron, 2012, vol. 68, p. 8539.

    Article  CAS  Google Scholar 

  10. Barbier, V., Couty, F., and David, O.R.P., Tetrahedron, 2016, vol. 72, p. 5646.

    Article  CAS  Google Scholar 

  11. Kramer, H.J., Kessler, D., Hipler, U.C., Irlinger, B., Hort, W., Bodeker, R.H., Steglich, W., and Mayser, P., ChemBioChem, 2005, vol. 6, no. 12, p. 2290.

    Article  Google Scholar 

  12. Malassezia and the Skin. Science and Clinical Practice, Boekhout, T., Guého-Kellermann, E., Mayser, P., and Velegraki, A., Eds., Heidelberg, Springer, 2010.

  13. Human and Animal Relationships (The Mycota, vol. 6), Brakhage, A.A. and Zipfel, P.F., Eds., Berlin: Springer, 2008, 2nd ed.

  14. Gein, V.L., Gein, L.F., Sheptukha, M.A., and Voronina, E.V., Pharm. Chem. J., 2005, vol. 39, no. 10, p. 537.

    Article  CAS  Google Scholar 

  15. Gein, L.F., Doctoral (Pharm.) Dissertation, Perm, 2009.

    Google Scholar 

  16. Gein, V.L., Gein, L.F., Kuznetsova, E.D., and Aliev, Z.G., Chem. Heterocycl. Compd., 2005, vol. 41, p. 255.

    Article  CAS  Google Scholar 

  17. CrysAlisPro, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET), Agilent Technologies.

  18. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3.

    Article  Google Scholar 

  19. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. L. Gein.

Additional information

Original Russian Text © V.L. Gein, O.V. Bobrovskaya, M.V. Dmitriev, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 6, pp. 881–886.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gein, V.L., Bobrovskaya, O.V. & Dmitriev, M.V. Synthesis of methyl 4-aryl-4-oxo-2-[(4-sulfamoylphenyl)amino]but-2-enoates and their reaction with ninhydrin. Russ J Org Chem 53, 898–903 (2017). https://doi.org/10.1134/S1070428017060148

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017060148

Navigation