Skip to main content
Log in

Synthesis and transformations of 6-acetyl-1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinoline

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

Abstract

By acylation of 1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinoline under the conditions of the Friedel–Crafts reaction its 6-acetyl derivative was obtained, which opens the access to new linearly designed 6-(pyrimidin-4-yl)-1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinolines.

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. Meunier, B., Acc. Chem. Res., 2007, vol. 41, no. 1, p. 69. doi 10.1021/ar7000843

    Article  Google Scholar 

  2. Cui, J.J., ASC Med. Chem. Lett., 2014, vol. 5, no. 4, p. 272. doi 10.1021/ml500091p

    Article  CAS  Google Scholar 

  3. Hu, Y., Furtmann, N., and Bajorath, J., J. Med. Chem., 2015, vol. 58, p. 30. doi 10.1021/jm5008159

    Article  CAS  Google Scholar 

  4. Hu, Y. and Bajorath, J., J. Med. Chem., 2015, vol. 58, p. 315. doi 10.1021/jm501237k

    Article  CAS  Google Scholar 

  5. Brown, C.W., Liu, S., Klucik, J., Berlin, K.D., Brennan, P.J., Kaur, D., and Benbrook, D.M., J. Med. Chem., 2004, vol. 47, no. 4, p. 1008. doi 10.1021/jm0303453

    Article  CAS  Google Scholar 

  6. Ivanov, Yu.A., Litvinov, V.I., Makarova, V., Osinin, V.V., Perevezentsev, V.A., Ryzhov, A.A., and Frolov, Yu., RF Patent 2372916, 2009.

  7. Fotie, J., Kaiser, M., Delfin, D.A., Manley, J., Reid, C.S., Paris, J.-M., Wenzler, T., Maes, L., Mahasenan, K.V., Li, C., and Werbovetz, K.A., J. Med. Chem., 2010, vol. 53, no. 3, p. 966. doi 10.1021/jm900723w

    Article  CAS  Google Scholar 

  8. Van Straten, N.C.R., Van Bercel, T.H.J., Demont, D.R., Karstens, W.-J.F., Merkx, R., Oosterom, J., Schulz, J., Van Someren, R.G., Timmers, C.M., and Van Zandvoort, P.M., J. Med. Chem., 2005, vol. 48, no. 6, p. 1697. doi 10.1021/jm049676l

    Article  Google Scholar 

  9. Vostrikova, A.V., Kalaev, V.N., Potapov, A.Yu., and Shikhaliev, Kh.S., Vestn. VSU, Ser. Khim., Biol., Farm., 2012, no. 1, p. 103.

    Google Scholar 

  10. Zalukaev, L.P. and Zheltukhina, T.I., Izv. Vuzov, Ser. Khim. Khim. Tekhnol., 1967, vol. 10, no. 4, p. 416.

    CAS  Google Scholar 

  11. Brown, J.P. and Tidd, B.K., J. Chem. Soc. (C), 1968, no. 9, p. 1075. doi 10.1039/J39680001075

    Google Scholar 

  12. Medvedeva, S.A., Krugovov, D.A., Mengele, E.A., and Shikhaliev, Kh.S., Vestn. VSU, Ser. Khim., Biol., Farm., 2013, no. 2, p. 49.

    Google Scholar 

  13. Shikhaliev, Kh.S., Shmyreva, Zh.V., Zalukaev, L.P., Ivanov, Yu.A., and Pokrovskaya, I.K., Author Certificate 1456417, 1988, Buyll. Izobret., 1989, no. 5.

  14. Eiden, F., Patzelt, G., and Buchborn, H., Arch. Pharm., 1989, vol. 322, no. 10, p. 589. doi 10.1002/ardp.19893221004

    Article  CAS  Google Scholar 

  15. Boykin, D.W., Kumar, A., Bajic, M., Xiao, G., Wilson, W.D., Bender, B.C., Mc. Curdi, D.R., Hall, G.E., and Tidwell, R.R., Eur. J. Med. Chem. 1997, vol. 32, p. 965. doi 10.1016/S0223-5234(97)89640-7

    Article  CAS  Google Scholar 

  16. Mustazza, C., Del Giudice, M.R., Borioni, A., and Gatta, F.J., Heterocycl. Chem., 2001, vol. 38, p. 1119. doi 10.1002/jhet.5570380516

    Article  CAS  Google Scholar 

  17. Bruno, O., Schenone, S., Ranise, A., Bondavalli, F., Filippeli, W., Falcone, G., Motola, G., and Mazzeo, F., Il Farmaco, 1999, vol. 54, p. 95. doi 10.1016/S0014-827X(98)00109-8

    Article  CAS  Google Scholar 

  18. Shikhaliev, Kh.S., Romanov, P.S. Shestakov, A.S., Stolpovskaya, N.V., Krysin, M.Yu., Potapov, A.Yu., and Proshin, A.N., Russ. Chem. Bull., 2016, vol. 65, no. 4, p. 1008. doi 10.1007/s11172-016-1404-1

    Article  CAS  Google Scholar 

  19. Dusza, J.P., Tomcufcik, A.S., and Albright, J.D., US Patent 4626538, 1986.

  20. Tseng, S.-S., Epstein, J.W., Brabander, H.J., and Francisco, G., J. Heterocycl. Chem., 1987, vol. 24, p. 837. doi 10.1002/jhet. 5570240357

    Article  CAS  Google Scholar 

  21. Joule, J.A. and Mills, K., Heterocyclic Chemistry, Hoboken Blakwell Science, 2000.

    Google Scholar 

  22. Shmyreva, Zh.V., 2,2,4-Trimetylgidrokhinoliny (2,2,4-Trimethylhydroquinolines), Voronezh: Voronezh Univ., 2000.

  23. King, H. and Tonkin, I.M., J. Chem. Soc., 1946, p. 1063. doi 10.1039/JR9460001063

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Potapov.

Additional information

Original Russian Text © А.Yu. Potapov, Kh.S. Shikhaliev, М.А. Potapov, L.V. Sapronova, F.I. Zubkov, Е.А. Kosheleva, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 7, pp. 1117–1122.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Potapov, A.Y., Shikhaliev, K.S., Potapov, M.A. et al. Synthesis and transformations of 6-acetyl-1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinoline. Russ J Gen Chem 87, 1510–1515 (2017). https://doi.org/10.1134/S1070363217070118

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217070118

Keywords

Navigation