Skip to main content
Log in

Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines

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

Abstract

N-Sulfonyl derivatives of 1,4-benzoquinone imine reacted with enamines to give 1,4-addition products and products of their subsequent cyclization, substituted 5-aminobenzofurans and 5-aminoindoles, depending on the solvent nature, electron-withdrawing power of the substituent on the quinone imine nitrogen atom, and enamine structure. The presence of strong electron-withdrawing trifluoromethanesulfonyl group on the quinone imine nitrogen atom favors formation of 1,4-addition products and benzofuran derivatives.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Titov, E.A., Grishchenko, A.S., and Podobuev, G.A., Zh. Org. Khim., 1972, vol. 8, p. 1260.

    CAS  Google Scholar 

  2. Titov, E.A., Grishchenko, A.S., Gura, L.A., and Kost, A.N., Chem. Heterocycl. Compd., 1973, vol. 9, p. 1311.

    Article  Google Scholar 

  3. Bogdanov, G.N., Titov, E.A., Shtol’ko, V.N., and Grishchenko, A.S., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972, vol. 21, p. 2747.

    Article  Google Scholar 

  4. Lyubchanskaya, V.M., Panisheva, E.K., Savina, S.A., Alekseeva, L.M., Shashkov, A.S., and Granik, V.G., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 1690.

    Article  CAS  Google Scholar 

  5. Avdeenko, A.P., Konovalova, S.A., Mikhailichenko, O.N., Yusina, A.L., Santalova, A.A., Palamarchuk, G.V., Zubatyuk, R.I., Shishkin, O.V., and Burmistrov, K.S., Russ. J. Org. Chem., 2011, vol. 47, p. 1169.

    Article  CAS  Google Scholar 

  6. Titov, E.A., Grishchenko, A.S., Prikhod’ko, V.I., and Kost, A.N., Zh. Org. Khim., 1974, vol. 10, p. 583.

    CAS  Google Scholar 

  7. Grishchenko, A.S., Prikhod’ko, V.I., Grishchenko, S.I., and Kost, A.N., Chem. Heterocycl. Compd., 1974, vol. 10, p. 1327.

    Article  Google Scholar 

  8. Trofimov, F.A., Tsyshkova, N.G., Nozdrich, V.I., and Grinev, A.N., Pharm. Chem. J., 1971, vol. 5, no. 1, p. 27.

    Article  Google Scholar 

  9. Grinev, A.N., Shvedov, V.I., Panisheva, E.K., Bogdanova, N.S., Nikolaeva, I.S., and Pershin, G.N., Pharm. Chem. J., 1971, vol. 5, no. 5, p. 247.

    Article  Google Scholar 

  10. Shvedov, V.I., Kurilo, G.N., and Grinev, A.N., Pharm. Chem. J., 1970, vol. 4, no. 9, p. 473.

    Article  Google Scholar 

  11. Mashkovskii, M.D., Lekarstva XXveka (Drugs of the XXth Century), Moscow Novaya Volna, 1998.

    Google Scholar 

  12. Granik, V.G., Osnovy meditsinskoi khimii (Fundamentals of Medicinal Chemistry), Moscow Vuzovskaya Kniga, 2001.

    Google Scholar 

  13. Avdeenko, A.P., Konovalova, S.A., Mikhailichenko, O.N., Shelyazhenko, S.V., Pirozhenko, V.V., and Yagupol’skii, L.M., Russ. J. Org. Chem., 2011, vol. 47, p. 510.

    Article  CAS  Google Scholar 

  14. Avdeenko, A.P., Konovalova, S.A., Mikhailichenko, O.N., Shelyazhenko, S.V., Pirozhenko, V.V., and Yagupol’skii, L.M., Russ. J. Org. Chem., 2012, vol. 48, p. 221.

    Article  CAS  Google Scholar 

  15. Domschke, G., Z. Chem. (Stuttgart, Ger.), 1966, vol. 6, p. 41.

    CAS  Google Scholar 

  16. Granik, V.G., Lyubchanskaya, V.M., and Mukhanova, T.I., Pharm. Chem. J., 1993, vol. 27, no. 6, p. 413.

    Article  Google Scholar 

  17. Mathieu, J. and Panico, R., Mecanismes reactionnels en chimie organique, Paris Hermann, 1972.

    Google Scholar 

  18. Filimonov, D.A., Lagunin, A.A., Gloriozova, T.A., Rudik, A.V., Druzhilovskii, D.S., Pogodin, P.V., and Poroikov, V.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 444.

    Article  CAS  Google Scholar 

  19. Avdeenko, A.P., Velichko, N.V., Romanenko, E.A., Pirozhenko, V.V., and Shurpach, V.I., Zh. Org. Khim., 1991, vol. 27, p. 2350.

    CAS  Google Scholar 

  20. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 349.

    Article  CAS  Google Scholar 

  21. Burmistrov, S.I. and Titov, E.A., Zh. Obshch. Khim., 1952, vol. 22, p. 999.

    CAS  Google Scholar 

  22. Avdeenko, A.P., Konovalova, S.A., and Ludchenko, O.N., Russ. J. Org. Chem., 2006, vol. 42, p. 683.

    Article  CAS  Google Scholar 

  23. Avdeenko, A.P. and Konovalova, S.A., Russ. J. Org. Chem., 2006, vol. 42, p. 669.

    Article  CAS  Google Scholar 

  24. Sheldrick, G.M., SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-Ray Diffraction Data. Rev.5.1, 1998.

  25. Brenans, P., C. R. Hebd. Seances Acad. Sci., 1914, vol. 157, p. 1155.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. P. Avdeenko.

Additional information

Original Russian Text © S.A. Konovalova, A.P. Avdeenko, V.V. Pirozhenko, A.L. Yusina, G.V. Palamarchuk, S.V. Shishkina, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 4, pp. 519–532.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Konovalova, S.A., Avdeenko, A.P., Pirozhenko, V.V. et al. Reaction of N-sulfonyl-1,4-benzoquinone imines with enamines. Russ J Org Chem 53, 525–538 (2017). https://doi.org/10.1134/S1070428017040054

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017040054

Navigation