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An efficient and practical synthesis of benzazolo[2,1-b]quinazolinones and triazolo[2,1-b]quinazolinones catalyzed by nano-sized NS-C4(DABCO-SO3H)2)·4Cl

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Abstract

In this study, 4,4′-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium)tetrachloride (NS-C4(DABCO-SO3H)2)·4Cl is used as a nano-sized Brönsted acid catalyst for the efficient and preferment synthesis of benzazolo[2,1-b]quinazolinones and triazolo[2,1-b]quinazolinones derivatives. This protocol has many advantages including mild reaction conditions, acceptable reaction times, high yields and easy work-up of the products and reusability of the catalyst.

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References

  1. J. Zhu, H. Bienayme, Multicomponent Reactions, 1st edn. (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  2. N. Isambert, M.M.S. Duque, J. Plaquevent, Y. Genisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 40, 1347 (2011)

    Article  CAS  Google Scholar 

  3. M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.H. Lee, J. Med. Chem. 43, 4479 (2000)

    Article  CAS  Google Scholar 

  4. Y. Xia, Z.Y. Yang, M.J. Hour, S.C. Kuo, P. Xia, K.F. Bastow, Y. Nakanishi, P. Namboothiri, T. Hackle, E. Hamel, K.H. Lee, Bioorg. Med. Chem. Lett. 11, 1193 (2001)

    Article  CAS  Google Scholar 

  5. F. Kato, H. Kimura, M. Omatsu, K. Yamamoto, R. Miyamoto, European Patent Application, WO 02/040485 (2002)

  6. B. McMaster, Anti-Inflammatory Compositions and Methods of Use, WO Patent 03105857, December 24 (2003)

  7. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 51, 3457 (2007)

    Article  Google Scholar 

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

    CAS  Google Scholar 

  9. S. Shigeta, S. Mori, M. Baba, M. Hosoya, N. Mochizuki, T. Chiba, E. De Clercq, Antivir. Chem. Chemother. 3, 171 (1992)

    Article  CAS  Google Scholar 

  10. Z.M. Nofal, H.H. Fahmy, H.S. Mohamed, Arch. Pharm. Res. 25, 28 (2002)

    Article  CAS  Google Scholar 

  11. A. Hafez, A.A. Monem, Arch. Pharm. Res. 30, 678 (2007)

    Article  Google Scholar 

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

    CAS  Google Scholar 

  13. D. Chai, D. M. Fitch, Propyl Hydroxylase Inhibitors, WO Patent 09039322 A1, March (2009)

  14. W.H.W. Lunn, R.W. Harper, R.L. Stone, J. Med. Chem. 14, 1069 (1971)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  17. V.V. Lipson, S.M. Desenko, V.V. Borodina, M.G. Shirobokova, Russ. J. Org. Chem. 41, 114 (2005)

    Article  CAS  Google Scholar 

  18. O.V. Fedorova, M.S. Zhidovinova, G.L. Rusinov, I.G. Ovchinnikova, Russ. Chem. Bull. 52, 1768 (2003)

    Article  CAS  Google Scholar 

  19. B. Insuasty, A. Salcedo, J. Quiroga, R. Abonia, M. Nogueras, J. Cobo, S. Salido, Heterocycl. Commun. 10, 399 (2004)

    CAS  Google Scholar 

  20. A. Shaabani, E. Farhangi, A. Rahmati, Comb. Chem. High Throughput Screen. 9, 771 (2006)

    Article  CAS  Google Scholar 

  21. A.E. Mourad, A.A. Aly, H.H. Farag, E.A. Beshr, Beilstein J. Org. Chem. 3, 11 (2007)

    Article  Google Scholar 

  22. Q. Shao, Sh Tu, Ch. Li, L. Cao, D. Zhou, Q. Wang, B. Jiang, Y. Zhang, W. Hao, J. Heterocycl. Chem. 45, 411 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  25. M.M. Heravi, F. Derikvand, L. Ranjbar, Synth. Commun. 40, 677 (2010)

    Article  CAS  Google Scholar 

  26. K. Kumari, D.S. Raghuvanshi, K.N. Singh, Org. Prep. Proced. Int. 44, 460 (2012)

    Article  CAS  Google Scholar 

  27. A. Shabani, E. Farhangi, Sh Shabani, Iran. J. Chem. Chem. Eng. 32, 3–10 (2013)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  29. A. Maleki, M. Aghaei, N. Ghamari, Chem. Lett. 44, 259 (2015)

    Article  CAS  Google Scholar 

  30. M.R. Mousavi, M.T. Maghsoodlou, Monatsh. Chem. 145, 1967 (2014)

    Article  CAS  Google Scholar 

  31. M.R. Mousavi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, J. Iran. Chem. Soc. 12, 1419 (2015)

    Article  CAS  Google Scholar 

  32. M.R. Mousavi, M.T. Maghsoodlou, J. Iran. Chem. Soc. 12, 743 (2015)

    Article  CAS  Google Scholar 

  33. G.M. Ziarani, A. Badiei, Z. Aslani, N. Lashgari, Arab. J. Chem. 8, 54 (2015)

    Article  Google Scholar 

  34. O. Goli-Jolodar, F. Shirini, J. Iran, Chem. Soc. 13, 1077 (2016)

    CAS  Google Scholar 

  35. M. Abedini, F. Shirini, M. Mousapour, O. Goli-Jolodar, Res. Chem. Intermed. (2016). doi:10.1007/s11164-016-2456-4

    Google Scholar 

  36. O. Goli-Jolodar, F. Shirini, M. Seddighi, RSC Adv. 6, 26026 (2016)

    Article  CAS  Google Scholar 

  37. F. Shirini, O. Goli Jolodar, J. Mol. Catal. A Chem. 356, 61 (2012)

    Article  CAS  Google Scholar 

  38. F. Shirini, M. Mamaghani, M. Seddighi, Catal. Commun. 36, 31 (2013)

    Article  CAS  Google Scholar 

  39. F. Shirini, NGh Khaligh, J. Mol. Liq. 177, 386 (2013)

    Article  CAS  Google Scholar 

  40. F. Shirini, NGh Khaligh, S. Akbari-Dadamahaleh, J. Mol. Catal. A Chem. 365, 15 (2012)

    Article  CAS  Google Scholar 

  41. F. Shirini, P.N. Moghadam, S. Moayediab, M. Seddighi, RSC Adv. 4, 38581 (2014)

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to the University of Guilan Research Council for the partial support of this work.

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Correspondence to Farhad Shirini.

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Goli-Jolodar, O., Shirini, F. An efficient and practical synthesis of benzazolo[2,1-b]quinazolinones and triazolo[2,1-b]quinazolinones catalyzed by nano-sized NS-C4(DABCO-SO3H)2)·4Cl. J IRAN CHEM SOC 14, 2275–2286 (2017). https://doi.org/10.1007/s13738-017-1164-3

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  • DOI: https://doi.org/10.1007/s13738-017-1164-3

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