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Synthesis of some new heterocycles containing quinazoline moiety

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Abstract

The presented herein synthesis of new quinazolines and quinazolino[3,4-a]quinazolines started from 2-amino-N-alkylbenzamides. Reaction of 2-amino-N-alkylbenzamides with 2-nitrobenzaldehyde followed by reduction using Zn afforded the corresponding 3-alkyl-2-(2-aminophenyl)-2,3-dihydroquinazolin-4(1H)-ones. Cyclization of the later compounds with carbon disulfide followed by methyl iodide, triethyl orthoformate or dimethyl acetylenedicarboxylate (DMAD) gave new quinazolino[3,4-a]quinazoline derivatives that were characterized on the basis of FT-IR, 1H, and 13C NMR spectra, and microanalytical data. In the case of reaction with DMAD, 2D nuclear Overhauser effect (2D-NOESY) spectrum together with comparison of the experimental and calculated chemical shifts at the B3LYP/6-311+G(d,p) level of theory were also used to identify the correct stereoisomer.

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References

  1. Tseng, M.-C., Chu, Y.-W., Tsai, H.-P., Lin, C.-M., Hwang, J., and Chu, Y.-H., Org. Lett., 2011, vol. 13, p. 920. doi 10.1021/ol1029707

    Article  CAS  Google Scholar 

  2. Dai, J.-R., Carte, B.K., Sidebottom, P.J., Yew, A.L.S., Ng, S.-B., Huang, Y., and Butler, M.S., J. Nat. Prod., 2001, vol. 64, p. 125. doi 10.1021/np000381u

    Article  CAS  Google Scholar 

  3. Jao, C.-W., Lin, W.-C., Wu, Y.-T., and Wu, P.-L., J. Nat. Prod., 2008, vol. 71, p. 1275. doi 10.1021/np800064w

    Article  CAS  Google Scholar 

  4. Li, P.-C., Liu, G., Cao, K., Sun, L., and Wen, Q.-W., Chin. Pharm. J., 2016, vol. 51, p. 867. doi 10.11669/cpj.2016.11.002

    CAS  Google Scholar 

  5. Boshta, N.M., El-Essawy, F.A., Ammar, R.M., Ismail, A.E.-H., and Wahba, N.E., Monatsh. Chem., 2016, vol. 147, p. 2031. doi 10.1007/s00706-016-1710-1

    Article  CAS  Google Scholar 

  6. Reddy, P.S., Venugopala, K.N., Rao, G.K., and Sanjay Pai, P.N., Indian J. Heterocycl. Chem., 2007, vol. 16, p. 243.

    CAS  Google Scholar 

  7. Liu, J., Liu, Y., Jian, J., and Bao, X., Chin. J. Org. Chem., 2013, vol. 33, p. 370. doi 10.6023/cjoc201209023

    Article  CAS  Google Scholar 

  8. Pathak, S.R., Malhotra, V., Nath, R., and Shanker, K., Cent. Nerv. Syst. Agents Med. Chem., 2014, vol. 14, p. 34. doi 10.2174/1871524914666140825144729

    Article  CAS  Google Scholar 

  9. Wang, Z., Wang, M., Yao, X., Li, Y., Tan, J., Wang, L., Qiao, W., Geng, Y., Liu, Y., and Wang, Q., Eur. J. Med. Chem., 2012, vol. 53, p. 275. doi 10.1016/j.ejmech.2012.04.010

    Article  CAS  Google Scholar 

  10. Chen, M.-H., Wang, X.-B., Tang, B.-C., and Zhang, X., Chem. Pap., 2016, vol. 70, p. 1521. doi 10.1515/chempap-2016-0090

    CAS  Google Scholar 

  11. Yu, C.-W., Chang, P.-T., Hsin, L.-W., and Chern, J.-W., J. Med. Chem., 2013, vol. 56, p. 6775. doi 10.1021/jm400564j

    Article  CAS  Google Scholar 

  12. Zhu, S., Wang, J., Chandrashekar, G., Smith, E., Liu, X., and Zhang, Y., Eur. J. Med. Chem., 2010, vol. 45, p. 3864. doi 10.1016/j.ejmech.2010.05.040

    Article  CAS  Google Scholar 

  13. Wang, R., Chai, W.-M., Yang, Q., Wei, M.-K., and Peng, Y., Bioorg. Med. Chem., 2016, vol. 24, p. 4620. doi 10.1016/j.bmc.2016.07.068

    Article  CAS  Google Scholar 

  14. Mohd Siddique, M.U., McCann, G.J.P., Sonawane, V.R., Horley, N., Gatchie, L., Joshi, P., Bharate, S.B., Jayaprakash, V., Sinha, B.N., and Chaudhuri, B., Eur. J. Med. Chem., 2017, vol. 130, p. 320. doi 10.1016/j.ejmech.2017.02.032

    Article  CAS  Google Scholar 

  15. Hei, Y.-Y., Xin, M., Zhang, H., Xie, X.-X., Mao, S., and Zhang, S.-Q., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 4408. doi 10.1016/j.bmcl.2016.08.015

    Article  CAS  Google Scholar 

  16. Lee, Y.S., Lee, B.H., Park, S.J., Kang, S.B., Rhim, H., Park, J.Y., Lee, J.H., Jeong, S.W., and Lee, J.Y., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 3379. doi 10.1016/j.bmcl.2004.04.090

    Article  CAS  Google Scholar 

  17. Rhim, H., Lee, Y.S., Park, S.J., Chung, B.Y., and Lee, J.Y., Bioorg. Med. Chem. Lett., 2005, vo. 15, p. 283. doi 10.1016/j.bmcl.2004.10.078

    Article  CAS  Google Scholar 

  18. Venkateswarlu, S., Satyanarayana, M., Lakshmikanthan, V., and Siddaiah, V., J Heterocycl Chem., 2015, vol. 52, p. 1631. doi 10.1002/jhet.2258

    Article  CAS  Google Scholar 

  19. Mohammadhosseini, N., Saeedi, M., Moradi, S., Mahdavi, M., Firuzi, O., Foroumadi, A., and Shafiee, A., Turk. J. Chem., 2017, vol. 41, p. 125. doi 10.3906/kim-1512-80

    Article  CAS  Google Scholar 

  20. Venkateswarlu, S., Satyanarayana, M., Ravikiran, P., and Vijayakumar, A., Tetrahedron Lett., 2013, vol. 54, p. 4512. 10.1016/j.tetlet.2013.06.060

    Article  CAS  Google Scholar 

  21. Mohammadhosseini, N., Moradi, S., Khoobi, M., and Shafiee, A., J. Heterocycl. Chem., 2016, vol. 53, p. 1595. doi 10.1002/jhet.2470

    Article  CAS  Google Scholar 

  22. Shafii, B., Saeedi, M., Mahdavi, M., Foroumadi, A., and Shafiee, A., Synth. Commun., 2014, vol. 44, p. 215. doi 10.1080/00397911.2013.800211

    Article  CAS  Google Scholar 

  23. Mahdavi, M., Lotfi, V., Saeedi, M., Kianmehr, E., and Shafiee, A., Mol. Divers., 2016, vol. 20, p. 677. doi 10.1007/s11030-016-9675-x

    Article  CAS  Google Scholar 

  24. Seifi, N., Zahedi-Niaki, M.H., Barzegari, M.R., Davoodnia, A., Zhiani, R., and Aghaei Kaju, A., J. Mol. Catal. A Chem., 2006, vol. 260, p. 77. doi 10.1016/j.molcata.2006.06.043

    Article  CAS  Google Scholar 

  25. 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.2007.07.024

    Article  CAS  Google Scholar 

  26. Davoodnia, A., Bakavoli, M., Bashash, M., Roshani, M., and Zhiani, R. Turk. J. Chem., 2007, vol. 31, p. 599.

    CAS  Google Scholar 

  27. 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.2007.09.004

    Article  CAS  Google Scholar 

  28. Davoodnia, A., Bakavoli, M., Mohseni, S., and Tavakoli-Hoseini, N. Monatsh. Chem., 2008, vol. 139, p. 963. doi 10.1007/s00706-007-0844-6

    Article  CAS  Google Scholar 

  29. Nakhaei, A. Davoodnia A., and Yadegarian, S., Russ. J. Gen. Chem., 2016, vol. 86, p. 2870. doi 10.1134/S1070363216120537

    Article  CAS  Google Scholar 

  30. Fattahi, M., Davoodnia, A., and Pordel, M., Russ. J. Gen. Chem., 2017, vol. 87, no. 4, p. 863. doi 10.1134/S1070363217040326

    Article  CAS  Google Scholar 

  31. Ameli, S., Davoodnia, A., Pordel, M., and Behmadi, H., J. Heterocycl. Chem., 2017, vol. 54, p. 1437. doi 10.1002/jhet.2729

    Article  CAS  Google Scholar 

  32. Vazirimehr, S., Davoodnia, A., Nakhaei-Moghaddam, M., and Tavakoli-Hoseini, N., Heterocycl. Commun., 2017, vol. 23, p. 65. doi 10.1515/hc-2016-0164

    Article  CAS  Google Scholar 

  33. Mohammadhosseini, N., Moradi, S., Khoobi, M., and Shafiee, A., J. Heterocycl. Chem., 2016, vol. 53, p. 1595. doi 10.1002/jhet.2470

    Article  CAS  Google Scholar 

  34. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery Jr, J.A., Vreven, 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 B. 05, Gaussian, Inc., Pittsburgh, PA, USA, 2003.

    Google Scholar 

  35. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785. doi 10.1103/PhysRevB.37.785

    Article  CAS  Google Scholar 

  36. Ditchfield, R., Mol. Phys., 1974, vol. 27, p. 789. doi 10.1080/00268977400100711

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, 9175687119, Iran

    F. Tajfirooz, A. Davoodnia, M. Pordel, M. Ebrahimi & S. A. Beyramabadi

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  1. F. Tajfirooz
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  2. A. Davoodnia
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  3. M. Pordel
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  4. M. Ebrahimi
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  5. S. A. Beyramabadi
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Correspondence to A. Davoodnia.

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Tajfirooz, F., Davoodnia, A., Pordel, M. et al. Synthesis of some new heterocycles containing quinazoline moiety. Russ J Gen Chem 87, 2429–2435 (2017). https://doi.org/10.1134/S1070363217100255

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  • DOI: https://doi.org/10.1134/S1070363217100255

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