Russian Journal of General Chemistry

, Volume 87, Issue 12, pp 2961–2965 | Cite as

Synthesis of New Functionalized 1,4-Dihydroquinolines and Pyrimido[4,5-b]quinolines

  • F. Khoramdelan
  • A. Davoodnia
  • M. R. Bozorgmehr
  • M. Ebrahimi
Letters to the Editor
  • 3 Downloads

Abstract

The reaction of N-alkylisatoic anhydrides with malononitrile in pyridine led to formation of new 2-amino-1-alkyl-4-oxo-1,4-dihydroquinoline-3-carbonitriles. Following treatment of these compounds with an excess of aliphatic carboxylic acids in the presence of POCl3 under reflux gave novel 2,10-dialkylpyrimido[4,5-b]quinoline-4,5(3H,10H)-diones with high yields. It is probable that synthesis of the latter products proceed via the tandem intramolecular Pinner–Dimroth rearrangement. All synthesized compounds were characterized by spectral and microanalytical data.

Keywords

dihydroquinoline pyrimido[4,5-b]quinoline POCl3 carboxylic acids 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Abdellatif, K.R.A., Abdelall, E.K.A., Abdelgawad, M.A., Amin, D.M.E., and Omar, H.A., Med. Chem. Res., 2017, vol. 26, p. 929. doi 10.1007/s00044-017-1798-9CrossRefGoogle Scholar
  2. 2.
    Singh, S.K., and Singh, S., Int. J. Pharm. Sci. Rev. Res., 2014, vol. 25, p. 295. doi Not availableGoogle Scholar
  3. 3.
    Wen, X., Wang, S.-B., Liu, D.-C., Gong, G.-H., and Quan, Z.-S., Med. Chem. Res., 2015, vol. 24, p. 2591. doi 10.1007/s00044-015-1323-yCrossRefGoogle Scholar
  4. 4.
    Khidre, R.E., Abdel-Wahab, B.F., and Abdel-Rehem Badria, F., Lett. Drug Des. Discovery, 2011, vol. 8, p. 640. doi 10.2174/157018011796235194CrossRefGoogle Scholar
  5. 5.
    Zemtsova, M.N., Zimichev, A.V., Trakhtenberg, P.L., Klimochkin, Y.N., Leonova, M.V., Balakhnin, S.M., Bormotov, N.I., Serova, O.A., and Belanov, E.F., Pharm. Chem. J., 2011, vol. 45, p. 267. doi 10.1007/s11094-011-0613-zCrossRefGoogle Scholar
  6. 6.
    Ashok, D., Ganesh, A., Vijaya Lakshmi, B., and Ravi, S., Russ. J. Gen. Chem., 2014, vol. 84, p. 1237. doi 10.1134/S1070363214060309CrossRefGoogle Scholar
  7. 7.
    Muruganantham, N., Sivakumar, R., Anbalagan, N., Gunasekaran, V., and Leonard, J.T., Biol. Pharm. Bull., 2004, vol. 27, p. 1683. doi 10.1248/bpb.27.1683CrossRefGoogle Scholar
  8. 8.
    Ramiz, M.M.M., El-Sayed, W.A., Hagag, E., and Abdel-Rahman, A.A.H., J. Heterocycl. Chem., 2011, vol. 48, p. 1028. doi 10.1002/jhet.686CrossRefGoogle Scholar
  9. 9.
    Atapour-Mashhad, H., Tayarani-Najaran, Z., Davoodnia, A., Moloudi, R., and Mousavi, S.H., Drug Chem. Toxicol., 2011, vol. 34, p. 271. doi 10.3109/01480545.2010.545066CrossRefGoogle Scholar
  10. 10.
    Desai, N.C., Kotadiya, G.M., and Trivedi, A.R., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 3126. doi 10.1016/j.bmcl.2014.05.002CrossRefGoogle Scholar
  11. 11.
    Chen, Q., Zhu, X., Jiang, L., Yang, L.M., and Fu, G., Eur. J. Med. Chem., 2008, vol. 43, p. 595. doi 10.1016/j.ejmech.2007.04.021CrossRefGoogle Scholar
  12. 12.
    Deshmukh, M.B., Salunkhe, S.M., Patil, D.R., and Anbhule, P.V., Eur. J. Med Chem., 2009, vol. 44, p. 2651. doi 10.1016/j.ejmech.2008.10.018CrossRefGoogle Scholar
  13. 13.
    El-Gazzar, A.B.A., Gaafar, A.M., Youssef, M.M., Abu-Hashem, A.A., and Badria, F.A., Phosphorus, Sulfur Silicon Relat. Elem., 2007, vol. 182, p. 2009. doi 10.1080/10426500701369864CrossRefGoogle Scholar
  14. 14.
    El-Gazzar, A.B.A., Hafez, H.N., Abu-Hashem, A.A., and Aly, A.S., Phosphorus, Sulfur Silicon Relat. Elem., 2009, vol. 184, p. 379. doi 10.1080/10426500802167027CrossRefGoogle Scholar
  15. 15.
    Hafez, H.N., Al-Hussain, S.A., and El-Gazzar, A.-R.B.A., Croat. Chem. Acta, 2016, vol. 89, p. 285. doi 10.5562/cca2912CrossRefGoogle Scholar
  16. 16.
    Tabatabaeian, K., Shojaei, A.F., Shirini, F., Hejazi, S.Z., and Rassa, M., Chin. Chem. Lett., 2014, vol. 25, p. 308. doi 10.1016/j.cclet.2013.10.021CrossRefGoogle Scholar
  17. 17.
    Jourshari, M.S., Mamaghani, M., Tabatabaeian, K., Shirini, F., Rassa, M., and Langhari, H., Lett. Org. Chem., 2012, vol. 9, p. 664. doi 10.2174/157017812803521207CrossRefGoogle Scholar
  18. 18.
    Davoodnia, A., Behmadi, H., Zare-Bidaki, A., Bakavoli, M., and Tavakoli-Hoseini, N., Chin. Chem. Lett., 2007, vol. 18, p. 1163. doi 10.1016/j.cclet.2007.07.024CrossRefGoogle Scholar
  19. 19.
    Davoodnia, A., Bakavoli, M., Bashash, M., Roshani, M., and Zhiani, R., Turk. J. Chem., 2007, vol. 31, p. 599.Google Scholar
  20. 20.
    Davoodnia, A., Roshani, M., Saleh Nadim, E., Bakavoli, M., and Tavakoli Hoseini, N., Chin. Chem. Lett., 2007, vol. 18, p. 1327. doi 10.1016/j.cclet.2007.09.004CrossRefGoogle Scholar
  21. 21.
    Davoodnia, A., Bakavoli, M., Mohseni, S., and Tavakoli-Hoseini, N., Monatsh. Chem., 2008, vol. 139, p. 963. doi 10.1007/s00706-007-0844-6CrossRefGoogle Scholar
  22. 22.
    Nakhaei, A. Davoodnia A., and Yadegarian, S., Russ. J. Gen. Chem., 2016, vol. 86, p. 2870. doi 10.1134/S1070363216120537CrossRefGoogle Scholar
  23. 23.
    Vazirimehr, S., Davoodnia, A., Nakhaei-Moghaddam, M., and Tavakoli-Hoseini, N., Heterocycl. Commun., 2017, vol. 23, p. 65. doi 10.1515/hc-2016-0164CrossRefGoogle Scholar
  24. 24.
    Ameli, S., Davoodnia, A., Pordel, M., and Behmadi, H., J. Heterocycl. Chem., 2017, vol. 54, p. 1437. doi 10.1002/jhet.2729CrossRefGoogle Scholar
  25. 25.
    Fattahi, M., Davoodnia, A., and Pordel, M., Russ. J. Gen. Chem., 2017, vol. 87, p. 863. doi 10.1134/S1070363217040326CrossRefGoogle Scholar
  26. 26.
    D’Souza, A.M., Spiccia, N., Basutto, J., Jokisz, P., Wong, L.S.-M., Meyer, A.G., Holmes, A.B., White, J.M., and Ryan, J.H., Org. Lett., 2011, vol. 13, p. 486. doi 10.1021/ol102824kCrossRefGoogle Scholar
  27. 27.
    Wube, A.A., Bucar, F., Hochfellner, C., Blunder, M., Bauer, R., and Hüfner, A., Eur. J. Med. Chem., 2011, vol. 46, p. 2091, doi 10.1016/j.ejmech.2011.02.062CrossRefGoogle Scholar
  28. 28.
    Tang, J.-H., Shi, D.-X., Zhang, L.-J., Zhang, Q., and Li, J.-R., Synth. Commun., 2010, vol. 40, p. 632. doi 10.1080/00397910902908822CrossRefGoogle Scholar
  29. 29.
    Chai, H., Li, J., Yang, L., Lu, H., Qi, Z., and Shi, D., RSC Adv., 2014, vol. 4, p. 44811. doi 10.1039/c4ra08031aCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • F. Khoramdelan
    • 1
  • A. Davoodnia
    • 1
  • M. R. Bozorgmehr
    • 1
  • M. Ebrahimi
    • 1
  1. 1.Department of Chemistry, Mashhad BranchIslamic Azad UniversityMashhadIran

Personalised recommendations