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Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives

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Abstract

A highly efficient and general method is applied for the multicomponent synthesis of quinazolinone derivatives from cyclocondensation of aromatic aldehydes and dimedone with 2-amino benzimidazole or 3-amino-1,2,4-triazole using nano-SiO2 as a catalyst in acetonitrile at room temperature. In this method, nano-SiO2 was used as a green and reusable catalyst. This synthetic method provides several advantages including excellent yields, short reaction times, simple workup, mild conditions and inexpensiveness, green, and recyclable.

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References

  1. E.M. Gordon, R.W. Barret, W.I. Dower, S.P. Fodor, M.A. Gallop, J. Med. Chem. 37, 1385 (1994)

    Article  CAS  Google Scholar 

  2. M.A. Gallop, R.W. Barret, W.J. Dower, S.P. Fodor, E.M. Gordon, J. Med. Chem. 37, 1233 (1994)

    Article  CAS  Google Scholar 

  3. A. Golisade, J. Wiesner, C. Herforth, H. Joma, A. Link, Bioorg. Med. Chem. 10, 769 (2002)

    Article  CAS  Google Scholar 

  4. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)

    Article  CAS  Google Scholar 

  5. A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39, 3168 (2000)

    Article  CAS  Google Scholar 

  6. A. Shaabani, A. Rahmati, A.H. Rezayan, H.R. Khavasi, J. Iran. Chem. Soc. 8, 24 (2011)

    Article  CAS  Google Scholar 

  7. A. Shaabani, A. Rahmati, A.H. Rezayan, M. Darvishi, Z. Badri, A. Sarvari, QSAR Comb. Sci. 26, 973 (2007)

    Article  CAS  Google Scholar 

  8. A. Monge, J.A. Palop, J.C.D. Castillo, J.M. Caldero, J. Roca, G. Romero, J.D. Rio, B. Lasheras, J. Med. Chem. 36, 2745 (1993)

    Article  CAS  Google Scholar 

  9. K. Toshima, R. Takano, T. Ozawa, S. Matsumara, Chem. Commun. 3, 212 (2002)

    Article  Google Scholar 

  10. B. Dowlati, D. Nematollahi, M.R. Othman, Int. J. Electrochem. Sci. 7, 5990 (2012)

    CAS  Google Scholar 

  11. Y.B. Kim, Y.H. Kim, J.Y. Park, S.K. Kim, Bioorg. Med. Chem. Lett. 14, 541 (2004)

    Article  CAS  Google Scholar 

  12. P.A.G.M. De Smet, Drugs 54, 801 (1997)

    Article  Google Scholar 

  13. J.D. Garcia, R. Somanathan, I.A. Rivero, G. Aguirre, L.H. Hellberg, Synth. Commun. 30, 2707 (2000)

    Article  CAS  Google Scholar 

  14. V.J. Ram, R.C. Srimal, D.S. Kushwaha, L. Mishra, J. Prakt. Chem. 332, 629 (1990)

    Article  CAS  Google Scholar 

  15. V. Alagarsamy, V.R. Solomon, G. Vanikavitha, V. Paluchamy, M. Ravichandran, A. Arnaldsujin, A. Thangathirupathy, S. Amuthalakshmi, R. Revathi, Biol. Pharm. Bull. 25, 1432 (2002)

    Article  CAS  Google Scholar 

  16. V. Alagarsamy, G. Murugananthan, R. Venkateshperumal, Biol. Pharm. Bull. 26, 1711 (2003)

    Article  CAS  Google Scholar 

  17. V. Alagarsamy, R. Venkatesaperumal, S. Vijayakumar, T. Angayarkanni, P. Pounammal, S. Senthilganesh, S. Kandeeban, Pharmazie. 57, 306 (2002)

    CAS  Google Scholar 

  18. V. Alagarsamy, Pharmazie 59, 753 (2004)

    CAS  Google Scholar 

  19. V. Alagarsamy, V.R. Solomon, M. Murugan, Bioorg. Med. Chem. 15, 4009 (2007)

    Article  CAS  Google Scholar 

  20. H. MannJen, H. Li Jiau, K. Sheng Chu, X. Yi Bastow, B. Kenneth, N. Y. Hamel, E. Lee, K. Hsiung, J. Med. Chem. 43, 4479 (2000)

  21. V. Alagarsamy, R. Revathi, S. Meena, K.V. Ramaseshu, S. Rajasekaran, E. De Clercq, Indian J. Pharm. Sci. 66, 459 (2004)

    CAS  Google Scholar 

  22. K.-C. Liu, M.-K. Hu, Arch. Pharm. 319, 188 (1986)

    Article  CAS  Google Scholar 

  23. T. Eicher, S. Hauptmann, Chemie der Heterocyclen (Georg Thieme, Stuttgart, New York, 1994), p. 398

    Google Scholar 

  24. V. Haridas, K. Lal, Y.K. Sharma, Tetrahedron Lett. 48, 4719 (2007)

    Article  CAS  Google Scholar 

  25. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457 (2007)

    Article  CAS  Google Scholar 

  26. A. Shaabani, A. Rahmati, E. Farhangi, A.H. Rezayan, Monatsh. Chem. 138, 615 (2007)

    Article  CAS  Google Scholar 

  27. M.M. Heravi, L. Ranjbar, F. Derikvand, B. Alimadadi, H.A. Oskooie, F.F. Bamoharram, Mol. Divers. 12, 181 (2008)

    Article  CAS  Google Scholar 

  28. G. Krishnamurthy, K.V. Jagannath, J. Chem. Sci. 125, 807 (2013)

    Article  CAS  Google Scholar 

  29. R.G. Puligoundla, S. Karnakanti, R. Bantu, N. Kommu, S.B. Kondra, L. Nagarapu, Tetrahedron Lett. 54, 2480 (2013)

    Article  CAS  Google Scholar 

  30. V.V. Lipson, S.M. Desenko, S.V. Shishkina, M.G. Shirobokova, O.V. Shishkin, V.D. Orlov, Chem. Heterocycl. Compd. 39, 1041 (2003)

    Article  CAS  Google Scholar 

  31. V.V. Lipson, S.M. Desenko, M.G. Shirobokova, V.V. Borodina, Chem. Heterocycl. Compd. 39, 1213 (2003)

    Article  CAS  Google Scholar 

  32. J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, Chin. Chem. Lett. 24, 921 (2013)

    Article  CAS  Google Scholar 

  33. J. Albadi, A. Mansournezhad, Z. Derakhshandeh, Chin. Chem. Lett. 24, 821 (2013)

    Article  CAS  Google Scholar 

  34. F.F. Bamoharram, M.M. Heravi, H. Teymouri, M. Zebarjad, A. Ahmadpour, Synth. React. Inorg. Met.-Org. Chem. 41, 1221 (2011)

    Article  CAS  Google Scholar 

  35. E. Rafiee, M. Khodayari, M. Kahrizi, R. Tayebee, J. Mol. Catal. A: Chem. 358, 121 (2012)

    Article  CAS  Google Scholar 

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Acknowledgments

The University of Sistan and Baluchestan is thanked for supporting this work.

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Correspondence to Malek Taher Maghsoodlou.

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Mousavi, M.R., Maghsoodlou, M.T. Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives. J IRAN CHEM SOC 12, 743–749 (2015). https://doi.org/10.1007/s13738-014-0533-4

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  • DOI: https://doi.org/10.1007/s13738-014-0533-4

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