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.
References
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.
Nanda, A.K., Ganduli, S., and Chakraborty, R., Molecules, 2007, vol. 12, no. 10, p. 2413, DOI: 10.3390/12102413.
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.
Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Moscow: Novaya Volna, 2012.
Omotowa, B.A. and Mesubi, M.A., Appl. Organomet. Chem., 1997, vol. 11, no. 1, p. 1. DOI: 10.1002/(SICI)1099-0739(199701).
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
Yu, Z.-G., Ding, W.-M., Ji, H.-R., Zhu, X.-Y., Chin. J. Org. Chem., 2010, vol. 30, no. 9, p. 1358.
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.
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.
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.
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. 127
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.
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.
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, no. 2, p. 785. DOI: 10.1103/PhysRevB.37.785.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. DOI: 10.1063/1.464913.
Ditchfield, R., Hehre, W.J., and Pople, J.A., J. Chem. Phys., 1971, vol. 54, no. 2, p. 724. DOI: 10.1063/1.1674902.
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).
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.
Porai-Koshits, B.A. and Kvitko, I.Ya., Zh. Obshch. Khim., 1962, vol. 32, no. 12, p. 4050.
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Original Russian Text © L.D. Popov, S.A. Borodkin, Yu.P. Tupolova, M.E. Kletskii, O.N. Burov, V.G. Vlasenko, A.S. Burlov, I.N. Shcherbakov, A.A. Zubenko, A.V. Derkun, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 7, pp. 1187–1194.
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Popov, L.D., Borodkin, S.A., Tupolova, Y.P. et al. 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). Russ J Gen Chem 85, 1706–1712 (2015). https://doi.org/10.1134/S1070363215070233
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DOI: https://doi.org/10.1134/S1070363215070233