Urea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
محورهای موضوعی : Iranian Journal of CatalysisAhmad Reza Momeni 1 , Heshmat Allah Samimi 2 , Reyhaneh Jahanian 3
1 - Faculty of Sciences, Shahrekord University, 115-381, Shahrekord, Iran.
2 - Faculty of Sciences, Shahrekord University, 115-381, Shahrekord, Iran.
3 - Faculty of Sciences, Shahrekord University, 115-381, Shahrekord, Iran.
کلید واژه: Alcohols, Urea-hydrogen peroxide, Silica phosphoric acid, Benzimidazoles,
چکیده مقاله :
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
[1] K.F. Ansari, C. Lal, Eur. J. Med. Chem. 44 (2009) 2294-2299.
[2] H. Goker, S. Ozden, S. Yildiz, D.W. Boykin, Eur. J. Med. Chem. 40 (2005) 1062-1069.
[3] S.M. Sondhi, N. Singh, A. Kumar, O. Lozach, L. Meijer, Bioorg. Med. Chem. 14 (2006) 3758-3765.
[4] M. Mor, F. Bordi, C. Silva, S. Rivara, V. Zuliani, F. Vacondio, M. Rivara, E. Barocelli, S. Bertoni, V. Ballabeni, F. Magnanini, M. Impicciatore, P.V. Plazzi, Bioorg. Med. Chem. 12 (2004) 663-674.
[5] M. Rivara, V. Zuliani, G. Cocconcelli, G. Morini, M. Comini, S. Rivara, M. Mor, F. Bordi, E. Barocelli, V. Ballabeni, S. Bertoni, P.V. Plazzi, Bioorg. Med. Chem. 14 (2006) 1413-1424.
[6] S. Demirayak, U. Abu Mohsen, A.C. Karaburun, Eur. J. Med. Chem. 37 (2002) 255-260.
[7] T. Yamori, A. Matsunaga, S. Sato, K. Yamazaki, A. Komi, K. Ishizu, I. Mita, H. Edatsugi, Y. Matsuba, K. Takezawa, O. Nakanishi, H. Kohno, Y. Nakajima, H. Komatsu, T. Andoh, T. Tsuruo, Cancer Res. 59 (1999) 4042-4049.
[8] W. Nawrocka, B. Sztuba, M.W. Kowalska, H. Liszkiewicz, J. Wietrzyk, A. Nasulewicz, M. Pelczynska, A. Opolski, Farmaco (Lausanne) 59 (2004) 83-91.
[9] D. Agic, M. Hranjec, N. Jajcanin, K. Starcevic, G. Karminski-Zamola, M. Abramic, Bioorg. Chem. 35 (2007) 153-169.
[10] M.A. Ismail, R. Brun, T. Wenzler, F.A. Tanious, W.D. Wilson, Boykin, D.W. Bioorg. Med. Chem. 12 (2004) 5405-2413.
[11] K. Starcevic, M. Krajl, K. Ester, I. Sabol, M. Grce, K. Pavelic, G. Karminski- Zamola, Bioorg. Med. Chem. 15 (2007) 4419-4426.
[12] Y.C. Chi, C.M. Sun, Synlett (2000) 591-594.
[13] W. Huang, R.M. Scarborough, Tetrahedron Lett. 40 (1999) 2665-2668.
[14] L.M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence, A.J. Blake, C. Wilson, M. Poliakoff, Green Chem. 5 (2003) 187-192.
[15] A.B. Allouma, K. Bougrin, M. Soufiaoui, Tetrahedron Lett. 44 (2003) 5935-5937.
[16] A.R. Momeni, S. Bagheri, Iranian J. Catal. 2 (2012) 31-35.
[17] B. Das, H. Holla, Y. Srinivas, Tetrahedron Lett. 48 (2007) 61-64.
[18] P. Ghosh, A. Mandal, Catal. Commun. 12 (2011) 744–747.
[19] H. Xiangming, M. Huiqiang, W. Yulu, ARKIVOC 2007 (xiii) 150-154.
[20] P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett. 4 (2006) 2557-2560.
[21] Z.H. Zhang, L. Yin, Y.M. Wang, Catal. Commun. 8 (2007) 1126–1131.
[22] K. Niknam, A. Fatehi-Raviz, J. Iran. Chem. Soc. 4 (2007) 438-443.
[23] C. Mukhopadhyay, P.K. Tapaswi, Tetrahedron Lett. 49 (2008) 6237-6240.
[24] T. Kondo, S. Yang, K.T. Huh, M. Kobayashi, S. Kotachi, Y. Watanabe, Chem. Lett. (1991) 1275-1278.
[25] V.R. Ruiz, A. Corma, M.J. Sabater, Tetrahedron Lett. 66 (2010) 730-735.
[26] K.D. Parghi, R.V. Jayaram, Catal. Commun. 11 (2010) 1205-1210.
[27] A.R. Momeni, M. Sadeghi, Appl. Catal. A 357 (2009) 100-105.
[28] A.R. Massah, M. Dabagh, M. Afshar, A.R. Momeni, H. Aliyan, H.J. Naghash, Turk. J. Chem. 31 (2007) 611-616.
[29] H. Aliyan, R. Fazaeli, H.J. Naghash, A.R. Massah, A.R. Momeni, Z. Iravani, Heteroatom Chem. 20 (2009) 325-331.
[30] Y.Wang, K.Sarris, D.R. Sauer, S.W. Djuric, Tetrahedron Lett. 473 (2006) 4823-4826.
[31] R.P. Karuvalam, M. Siji, N. Divia, K.R. Haridas J. Korean Chem. Soc. 54 (2010) 589-593.
[32] R.R. Nagawade, D.B. Shinde, Chin. Chem. Lett. 17 (2006) 453-456.
[33] M.A. Zolfigol, F. Shirini, K. Zamani, E. Ghofrani, S. Ebrahimi, Phosphorus Sulfur 179 (2004) 2177-2188.
[34] A.J. Fatiadi, Synthesis (1976) 65-104.
[35] H.J. Park, J.C. Lee, Synlett (2009) 79-80.
[36] C. Wilfred, R.J.K. Taylor, Synlett (2004) 1628-1630.
