Preparation, characterization, and application of 1,1-disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the synthesis of benzimidazole derivatives
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  • 作者:Farhad Shirini ; Masoumeh Abedini ; Mohadeseh Seddighi…
  • 关键词:[BiPy](SO3H)2Cl2 ; Ionic liquid ; Benzimidazoles ; Aldehydes ; Protected aldehydes
  • 刊名:Research on Chemical Intermediates
  • 出版年:2015
  • 出版时间:October 2015
  • 年:2015
  • 卷:41
  • 期:10
  • 页码:7683-7693
  • 全文大小:930 KB
  • 参考文献:1.M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S.B. Azimi, Zh. Asgari, A.Hasaninejad, C.R. Chimie 15, 719 (2012)
    2.A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 167, 69 (2012)CrossRef
    3.A. Zare, T. Yousofi, A.R. Moosavi-Zare, RSC Advances 2, 7988 (2012)CrossRef
    4.H.G.O. Alvim, T.B. de Lima, H.C.B. de Oliveira, F.C. Gozzo, J.L. de Macedo, P.V. Abdelnur, W.A. Silva, B.A.D. Neto, ACS Catal. 3, 1420 (2013)CrossRef
    5.J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)CrossRef
    6.H.R. Shaterian, M. Sedghipour, E. Mollashahi, Res. Chem. Intermed. (2013). doi:10.-007/?s11164-013-1043-1
    7.A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva, V.A. Anisimova, Pharm. Chem. J. 33, 232 (1999)CrossRef
    8.T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. BuckheitJr, C.J. Michejda, J. Med. Chem. 40, 4199.(1997)
    9.S.T. Huang, I.J. Hsei, C. Chen, Bioorg. Med. Chem. Lett. 14, 6106 (2006)CrossRef
    10.R.J. Alaimo, S.S. Pelosi, R. Freedman, J. Pharm. Sci. 67, 281 (1978)CrossRef
    11.Y. Luo, J. Yao, L. Yang, C. Feng, W. Tang, G. Wang, J. Zuo, W. Lu, Bioorg. Med. Chem. 18, 5048 (2010)CrossRef
    12.K.C.S. Achar, K.M. Hosamani, H.R. Seetharamareddy, Eur. J. Med. Chem. 45, 2048 (2010)CrossRef
    13.K.F. Ansari, C. Lal, Eur. J. Med. Chem. 44, 4028 (2009)CrossRef
    14.R. Lozytska, D. Chikhichin, V. Lozitsky, A. Fedchuk, V. Kuz’min, A. Artemenko, L. Shitikova, L. Mudrik, T. Gridina, E. Muratov, Antivir. Res. 74, 80 (2007)CrossRef
    15.N.T.A. Ghani, A.M. Mansour, J. Mol. Struct. 991, 108 (2011)CrossRef
    16.J. Jayabharathi, V. Thanikachalam, K. Jayamoorthy, R. Sathishkumar, Spectrochim. Acta A. 97, 384 (2012)CrossRef
    17.R.S. Pottorf, N.K. Chadha, M. Katkevics, V. Ozola, E. Suna, H. Ghane, T. Regberg, M.R. Player, Tetrahedron Lett. 44, 175 (2003)CrossRef
    18.H. Matsushita, S. Lee, M. Joung, B. Clapham, K.D. Janda, Tetrahedron Lett. 45, 313 (2004)CrossRef
    19.B. Karami, S. Nikoseresht, S. Khodabakhshi, Chin. J. Catal. 33, 298 (2010)CrossRef
    20.S. Khaksar, A. Heydari, M. Tajbakhsh, S.M. Vahdat, J. Fluor. Chem. 131, 1377 (2010)CrossRef
    21.G. Aridoss, K.K. Laali, Eur. J. Org. Chem. 15, 2827 (2011)CrossRef
    22.T.B. Kumar, C. Sumanth, A.V.D. Rao, D. Kalita, M.S. Rao, K.B.C. Sekhar, K.S. Kumar, M. Pal, RSC Adv. 2, 11510 (2012)CrossRef
    23.X. Wen, J.E. Bakali, R. Deprez-Poulain, B. Deprez, Tetrahedron Lett. 53, 2440 (2012)CrossRef
    24.M. Dabiri, P. Salehi, M. Baghbanzadeh, M. ShakouriNikcheh, Synth. Commun. 38, 4272 (2008)CrossRef
    25.D. Saha, A. Saha, B.C. Ranu, GreenChem. 11, 733 (2009)
    26.A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Z.H. Asgari, A. Hasaninejad, ScientiaIranica C 18, 1365 (2011)
    27.F. Shirini, A. Yahyazadeh, K. Mohammadi, Chin. Chem. Lett. 25, 341 (2014)CrossRef
    28.F. Shirini, A. Yahyazadeh, K. Mohammadi, N.G. Khaligh, C.R. Chimie 17, 370 (2014)
    29.F. Shirini, N.G. Khaligh, J. Mol. Liq. 177, 386 (2013)CrossRef
    30.F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, J. Mol. Catal. A: Chem. 15, 365 (2012)
    31.A.R. Moosavi-Zarea, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: General 467, 61 (2013)CrossRef
    32.H. Xing, T. Wang, Z. Zhou, Y. Dai, J. Mol. Catal. A: Chem. 264, 53 (2007)CrossRef
    33.Kh Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 54, 8055 (1998)CrossRef
    34.R.R. Nagawade, D.B. Shinde, Indian J. Chem. 46B, 349 (2007)
    35.S.B. Rathod, M.K. Lande, B.R. Arbad, Bull. Korean Chem. Soc. 31, 2835 (2010)CrossRef
    36.H. Eshghi, M. Rahimizadeh, A. Shiri, P. Sedaghat, Bull. Korean Chem. Soc. 33, 515 (2012)CrossRef
    37.L.S. Gadekar, B.R. Arbad, M.K. Lande, Chin. Chem. Lett. 21, 1053 (2010)CrossRef
    38.A. Teimouri, J. Mol. Cat. A: Chem. 373, 38 (2013)CrossRef
    39.S.E. López, J. Restrepo, B. Pérez, Sh Ortiz, J. Salazar, Bull. Korean Chem. Soc. 30, 1628 (2009)CrossRef
    40.P. Gogoi, D. Konwar, Tetrahedron Lett. 47, 79 (2006)CrossRef
    41.K. Bahrami, A. Nejatia, Green Chem. 12, 1237 (2010)CrossRef
    42.Y. Venkateswarlu, S. Ramesh Kumar, P. Leelavathi, Org. Med. Chem. Lett. 3(1), 2013 (2013). doi:10.-186/-191-2858-3-7 CrossRef
    43.R.S. Joshi, P.G. Mandhane, S.K. Dabhade, C.H.H. Gill, J. Chin. Chem. Soc. 57, 1227 (2010)CrossRef
    44.A. Teimouri, A.N. Chermahini, H. Salavati, L. Ghorbanian, J. Mol. Catal. A: Chem. 373, 38 (2013)CrossRef
    45.R. Ghorbani-Vaghei, H. Veisi, Mol. Divers. 14, 249 (2010)CrossRef
  • 作者单位:Farhad Shirini (1)
    Masoumeh Abedini (1)
    Mohadeseh Seddighi (1)
    Fatemeh Shaabani Arbosara (1)

    1. Department of Chemistry, College of Science, University of Guilan, Post Box 1914, 41335, Rasht, Iran
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Catalysis
    Physical Chemistry
    Inorganic Chemistry
  • 出版者:Springer Netherlands
  • ISSN:1568-5675
文摘
In this study, 2,2-bipyridine was treated with chlorosulfonic acid and 1,1-disulfo-[2,2-bipyridine]-1,1-diium chloride, [BiPy](SO3H)2Cl2, as a new ionic liquid catalyst was obtained and characterized with a variety of techniques including IR, 1H, and 13C NMR, Hammett acidity function as well as mass spectra method. After preparation and characterization, this ionic liquid was used as an efficient catalyst for the green and mild synthesis of benzimidazole derivatives. In addition, this reagent is efficiently able to catalyze the preparation of benzimidazole derivatives from the protected derivatives of aldehydes including oximes and semicarbazones. All reactions are performed under mild conditions in excellent yields. Keywords [BiPy](SO3H)2Cl2 Ionic liquid Benzimidazoles Aldehydes Protected aldehydes

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