Russian Journal of General Chemistry

, Volume 85, Issue 7, pp 1706–1712 | Cite as

Spectral and theoretical study of 2-methyl-3-{[(Z)-3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)methyl]amino}quinazolin-4-one and its complexes with metal ions M(II)

  • L. D. Popov
  • S. A. Borodkin
  • Yu. P. Tupolova
  • M. E. Kletskii
  • O. N. Burov
  • V. G. Vlasenko
  • А. S. Burlov
  • I. N. Shcherbakov
  • А. А. Zubenko
  • А. V. Derkun
Article

Abstract

2-Methyl-3-{[(Z)-3-methyl-5-oxo-1-phenylpyrazol-4-ylidene)methyl]amino}quinazolin-4-one was synthesized by condensation of 5-hydroxy-4-formyl-3-methyl-1-phenylpyrazole with N-amino-2-methylquinazolin-4-one and its structure and properties were studied by IR, 1H, 13C NMR, 2D 1H NMR (COSY) and electronic spectroscopy and mass-spectrometry. By the reaction of compound (III) with Cd(II), Zn(II), and Pb(II) acetates the intracomplex compounds of 1: 2 composition (metal: ligand) were obtained.

Keywords

enamines NMR spectroscopy electron spectroscopy quantum-chemical calculations 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kumar, S., Mishra, G., Singh, P., Jha, K.K., Khosa, R.L., and Gupta, S.K., Der Chemica Sinica, 2011, vol. 2, no. 4, p. 36.Google Scholar
  2. 2.
    Nanda, A.K., Ganduli, S., and Chakraborty, R., Molecules, 2007, vol. 12, no. 10, p. 2413, DOI: 10.3390/12102413.CrossRefGoogle Scholar
  3. 3.
    Panneerselvam, P., Ahmad, B.R., Sankar, R.D., and Kumar, R.N., Eur. J. Med. Chem., 2009, vol. 44, no. 5, p. 2328. DOI: 10.1016/j.ejmech.2008.04.010.CrossRefGoogle Scholar
  4. 4.
    Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2012.Google Scholar
  5. 5.
    Omotowa, B.A. and Mesubi, M.A., Appl. Organomet. Chem., 1997, vol. 11, no. 1, p. 1. DOI: 10.1002/(SICI)1099-0739(199701).CrossRefGoogle Scholar
  6. 6.
    Cushman, M., Jayaraman, M., Vroman, J.A., Fukunaga, A.K., Fox, B.M., Kohlhagen, G., Strumberg, D., and Pommier, Y., J. Med. Chem., 2000, vol. 43, p. 3665. DOI: 10.1021/jm000029d CrossRefGoogle Scholar
  7. 7.
    Yu, Z.-G., Ding, W.-M., Ji, H.-R., Zhu, X.-Y., Chin. J. Org. Chem., 2010, vol. 30, no. 9, p. 1358.Google Scholar
  8. 8.
    Prasad, K.S., Kumar, L.S., Chandan, S., Jayalakshmi, B., and Revanasiddappa, H.D., Spectrochim. Acta Part A, 2011, vol. 81, p. 276. DOI: 10.1016/j.saa.2011.06.010.Google Scholar
  9. 9.
    Gudasi, K.B., Vadavi, R.S., Shenov, R.V., Patil, S.A., and Nathaji, M., Transit. Metal. Chem., 2006, vol. 31, no. 1, p. 135. DOI: 10.1007/s11243-005-6363-6.CrossRefGoogle Scholar
  10. 10.
    Gudasi, K.B., Vadavi, R.S., Shenov, R.V., Patil, S.A., and Nathaji, M., Transit. Metal. Chem., 2005, vol. 30, no. 6, p. 661. DOI: 10.1007/s11243-005-4829-1.CrossRefGoogle Scholar
  11. 11.
    Shiva, P.K., Shiva, K.L., Melvin, P., Jayalakshmi, B., and Hosakere, D.R., Biointerface Res. Appl. Chem. Open Access J., 2011, vol. 1, no. 4, p. 127Google Scholar
  12. 12.
    Popov, L.D., Borodkin, S.A., Shcherbakov, I.N., Tkachenko, Y.N., Aleksandrov, G.G., Beloborodov, S.S., Zubenko, A.A., Kogan, V.A., and Maevskii, O.V., Russ. J. Gen. Chem., 2013, vol. 83, no. 7, p. 1376. DOI: 10.1134/S107036321307013X.CrossRefGoogle Scholar
  13. 13.
    Levchenkov, S.I., Shcherbakov, I.N., Popov, L.D., Uraev, A.I., Suponitskii, K.Yu., Zubenko, A.A., Ionov, A.M., and Kogan, V.A., J. Struct. Chem., 2015, vol. 56, no. 1, p. 113.CrossRefGoogle Scholar
  14. 14.
    Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, p. 785. DOI: 10.1103/PhysRevB.37.785.CrossRefGoogle Scholar
  15. 15.
    Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. DOI: 10.1063/1.464913.CrossRefGoogle Scholar
  16. 16.
    Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, no. 2, p. 724. DOI: 10.1063/1.1674902.CrossRefGoogle Scholar
  17. 17.
    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, Jr.T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision A.1, Gaussian, Inc., Pittsburgh PA, USA (2003).Google Scholar
  18. 18.
    Kumaradhas, P., Lakshmi, G.S., Sridhar, B., Selvam, P.P., and Saravanan, G., Acta Cryst. E, 2007, vol. 63, p. o4293. DOI: 10.1107/S1600536807047393.
  19. 19.
    Porai-Koshits, B.A. and Kvitko, I.Ya., Zh. Obshch. Khim., 1962, vol. 32, no. 12, p. 4050.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2015

Authors and Affiliations

  • L. D. Popov
    • 1
  • S. A. Borodkin
    • 1
  • Yu. P. Tupolova
    • 1
  • M. E. Kletskii
    • 1
  • O. N. Burov
    • 1
  • V. G. Vlasenko
    • 2
  • А. S. Burlov
    • 3
  • I. N. Shcherbakov
    • 1
  • А. А. Zubenko
    • 4
  • А. V. Derkun
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia
  2. 2.Institute of Physics of Southern Federal UniversityRostov-on-DonRussia
  3. 3.Research Institute of Physical and Organic Chemistry of Southern Federal UniversityRostov-on-DonRussia
  4. 4.North Caucasus Zonal Veterinary Research InstituteNovocherkasskRussia

Personalised recommendations