Skip to main content
Log in

Synthesis and transformations of new 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives

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

Abstract

Reactions of cyclohexane-1,3-diones with amines and aldehydes led to the formation of 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones containing alkylaryl, aryl, and hydroxy substituents in position 10. Transformations of 10-hydroxy-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under oxidation with nitrous acid, reduction with zinc powder, as well as on heating in aprotic solvents and acetic, phosphoric, and polyphosphoric acids, were studied. NMR spectra of 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones having different substituents in positions 9 and 10 were analyzed.

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. Vanag, G.Ya. and Stankevich, E.I., Zh. Obshch. Khim., 1960, vol. 30, p. 3287.

    Google Scholar 

  2. Nikolaeva, T.G., Shchekotikhin, Yu.M., Ponomarev, A.S., and Kriven’ko, A.P., Khim. Geterotsikl. Soedin., 2000, p. 475.

  3. Shchekotikhin, Yu.M., Getmanenko, Yu.A., Nikolaeva, T.G., and Kriven’ko, A.P., Khim. Geterotsikl. Soedin., 2001, p. 1344.

  4. Chebanov, V.A., Saraev, V.E., Kobzar’, K.M., Desenko, S.M., Orlov, V.D., and Gura, E.A., Khim. Geterotsikl. Soedin., 2004, p. 571.

  5. Loev, B., Goodman, M.M., Snader, K.M., Tedechi, R., and Macko, E., J. Med. Chem., 1974, vol. 17, p. 956.

    Article  CAS  Google Scholar 

  6. Shchekotikhin, Yu.M., Nikolaeva, T.G., Shub, G.M., and Kriven’ko, A.P., Khim.-Farm. Zh., 2001, vol. 35, p. 29.

    Google Scholar 

  7. Shchekotikhin, Yu.M. and Nikolaeva, T.G., Khim. Geterotsikl. Soedin., 2006, p. 32.

  8. Joule, J.A. and Smith, G.F., Heterocyclic Chemistry, London: Van Nostrand Reinhold, 1972.

    Google Scholar 

  9. Paquette, L.A., Principles of Modern Heterocyclic Chemistry, New York: W.A. Benjamin, 1968. Translated under the title Osnovy sovremennoi khimii geterotsiklicheskikh soedinenii, Moscow: Mir, 1971, p. 352.

    Google Scholar 

  10. Pyrko, A.N., Russ. J. Org. Chem., 2002, vol. 38, p. 1817.

    Article  CAS  Google Scholar 

  11. Dzvinchuk, I.B. and Tolmacheva, N.A., Khim. Geterotsikl. Soedin., 2001, p. 554.

  12. Hegde, V., Hung, C., Madhukar, P., Cunningham, R., Hopfner, T., and Thummel, R.P., J. Am. Chem. Soc., 1993, vol. 115, p. 872.

    Article  CAS  Google Scholar 

  13. Freimanis, Ya.F., Khimiya enaminoketonov, enaminoiminov, enaminotionov (Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones), Riga: Zinatne, 1974, p. 274.

    Google Scholar 

  14. Milliaresi, E.E., Ruchkin, V.E., Orlova, T.I., and Efremov, V.V., Dokl. Akad. Nauk SSSR, 1972, vol. 205, p. 353.

    CAS  Google Scholar 

  15. Bellamy, L.J., The Infra-red Spectra of Complex Molecules, London: Methuen, 1958.

    Google Scholar 

  16. Gutsulyak, Kh.V., Manzhara, V.S., Mel’nik, M.V., and Kalin, T.I., Zh. Prikl. Spektrosk., 2005, vol. 72, p. 454.

    Google Scholar 

  17. Minkin, V.I., Simkin, B.Ya., and Minyaev, R.M., Teoriya stroeniya molekul (Theory of Molecular Structure), Rostov-on-Don: Feniks, 1997.

    Google Scholar 

  18. Shanmugasundaram, P., Prabahar, K.J., and Ramakrishman, V.T., J. Heterocycl. Chem., 1993, vol. 30, p. 1003.

    CAS  Google Scholar 

  19. Pyrko, A.N., Khim. Geterotsikl. Soedin., 1996, p. 742.

  20. Bakibaev, A.A. and Filimonov, V.D., Zh. Org. Khim., 1991, vol. 27, p. 223.

    CAS  Google Scholar 

  21. Martin, N., Quinteiro, M., Seoane, C., Soto, J.L., Mora, A., Suarez, M., and Ochoa, E., J. Heterocycl. Chem., 1995, vol. 32, p. 235.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. N. Pyrko.

Additional information

Original Russian Text © A.N. Pyrko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 8, pp. 1227–1236.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pyrko, A.N. Synthesis and transformations of new 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives. Russ J Org Chem 44, 1215–1224 (2008). https://doi.org/10.1134/S1070428008080198

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428008080198

Keywords

Navigation