P. Ghosh, A. Mandal / Catalysis Communications 12 (2011) 744–747
[6] Y. Bai, J. Lu, Z. Shi, B. Yang, Synlett 12 (2001) 544–546.
747
Table 3
[7] E. Hasegawa, A. Yoneoka, K. Suzuki, T. Kato, T. Kitazume, K. Yangi, Tetrahedron 55
(1999) 12957–12968.
Recycling experiment using SDS.
[8] E. Bouwman, W.L. Driessen, J. Reedjik, Coord. Chem. Rev. 104 (1990) 143–172.
[9] M.A. Pujar, T.D. Bharamgoudar, Transition Met. Chem. 13 (1988) 423–425.
[10] G.D. Zhu, V.B. Gandhi, J. Gong, S. Thomas, Y. Luo, X. Liu, Y. Shi, V. Klinghofer, E.F.
Johnson, D. Frost, C. Donawho, K. Jarvis, J. Bouska, K.C. Marsh, S.H. Rosenberg, V.L.
Giranda, T.D. Penning, Bioorg. Med. Chem. Lett. 18 (2008) 3955–3958.
[11] Y. Ogino, N. Ohtake, Y. Nagae, K. Matsuda, M. Moriya, T. Suga, M. Ishikawa, M.
Kanesaka, Y. Mitobe, J. Ito, T. Kanno, A. Ishiara, H. Iwaasa, T. Ohe, A. Kanatani, T.
Fukami, Bioorg. Med. Chem. Lett. 18 (2008) 5010–5014.
Entry
No. of cycles
% Yield
1
2
3
4
5
6
0
1
2
3
4
5
92
87
82
78
72
68
[12] D.I. Shah, M. Sharma, Y. Bansal, G. Bansal, M. Singh, Eur. J. Med. Chem. 43 (2008)
1808–1812.
% Yield refers to the isolated yield of the compound after chromatography.
[13] M.R. Grimmet, in: A.R. Katritzky, C.W. Rees, K.T. Potts (Eds.), Comprehensive
Heterocyclic Chemistry, Pergamon Press, NewYork, 19848, Vol. 5.
[14] P.N. Preston, in: A. Weissberger, E.C. Taylor (Eds.), Chemistry, of Heterocyclic
Compounds, John Wiley and Sons, 19818, Vol. 40.
[15] L.M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence, A.J. Blake, C. Wilson, M.
Poliakoff, Green Chem. 5 (2003) 187–192.
[16] R.J. Perry, B.D. Wilson, J. Org. Chem. 58 (1993) 7016–7021.
[17] C.T. Brain, S.A. Brunton, Tetrahedron Lett. 43 (2002) 1893–1895.
[18] D. Anastasiou, E.M. Campi, H. Chaouk, W.R. Jackson, Tetrahedron 48 (1992)
7467–7478.
[19] D.L. Yang, D. Fokas, J.Z. Li, L.B. Yu, C.M. Baldino, Synthesis 37 (2005) 47–56.
[20] Z. Wu, P. Rea, G. Wickam, Tetrahedron Lett. 41 (2000) 9871–9874.
[21] For selected examples in selective synthesis of 2-substituted benzimidazole using
o-phenylenediamine and aldehyde. R. Trivedi, S.K. De, R.A. Gibbs, J. Mol. Catal. A:
Chem. 245 (2006) 8–11.
The reaction mixture was then allowed to stir at room temperature
with magnetic spinning bar. A foamy mass appeared immediately and
get settled like a precipitate. After the completion of the reaction, the
solid reaction mixture was washed with dichloromethane (5×4`) and
the washings were collected and evaporated under vacuum. The
crude product was then crystallized from ethanol. The desired
purified product was characterized by spectral (IR, 1H and 13C NMR)
data and compared to those reported in literature.
Acknowledgements
[22] P.L. Beaulieu, B. Hache, E. Von Moos, Synthesis 35 (2003) 1683–1692.
[23] K. Bahrami, M.M. Khodaei, I. Kavianinia, Synthesis 39 (2007) 547–550.
[24] K. Baharami, M.M. Khodaei, F. Naali, J. Org. Chem. 73 (2008) 6835–6837.
[25] H. Sharghi, M. Aberi, M.M. Doroodmand, Adv. Synth. Catal. 350 (2008) 2380.
[26] Y.X. Chen, L.F. Qian, W. Zhang, B. Han, Angew. Chem. Int. Ed. 47 (2008)
9330–9333.
Financial support from UGC, India was cordially acknowledged.
Appendix A. Supplementary data
[27] D. Saha, A. Saha, B.C. Ranu, Green Chem. 11 (2009) 733–737.
[28] For typical example in selective synthesis of 1,2-disubstituted benzimidazoles
using o-phenylenediamine and aldehyde. N.D. Kokare, J.N. Sangshetti, D.B. Shinde,
Synthesis (2007) 2829–2834.
Supplementary data to this article can be found online at doi:10.1016/
j.catcom.2011.01.005.
[29] P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett.
47 (2006) 2557–2560.
References
[30] M. Chakrabarty, R. Mukherjee, S. Karmakar, Y. Harigaya, Monatsh. Chem. 138
(2007) 1279–1282.
[31] V. Ravi, E. Ramu, K. Vljay, A.S. Rao, Chem. Pharm. Bull. 55 (2007) 1254–1257.
[32] J.S. Yadav, B.V.S. Reddy, K. Premalatha, K.S. Shankar, Can. J. Chem. 86 (2008)
124–132.
[33] M.A. Biasutti, E.B. Abuin, J.J. Silber, N.M. Correa, E.A. Lissi, Adv. Colloidal Interface
Sci. 136 (2008) 1–24.
[34] Y.Y. Peng, Q.P. Ding, Z. Li, P.G. Wang, J.P. Cheng, Tett. Lett. 44 (2003) 3871–3875.
[1] P.W. Erhardt, J. Med. Chem. 30 (1987) 231–237.
[2] G.L. Gravalt, B.C. Baguley, W.R. Wilson, W.A. Denny, J. Med. Chem. 37 (1994)
4338–4345.
[3] K.J. Soderlind, B. Gorodetsky, A.K. Singh, N. Bachur, G.G. Miller, J.W. Loun,
Anticancer Drug Des. 14 (1999) 19–25.
[4] J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, E.J. LaVoie, J. Med. Chem. 39 (1996) 992–998.
[5] T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit Jr., C.J. Michejda, J.
Med. Chem. 40 (1997) 4199–4207.