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Synthesis of 1-Alkyl-2-chloromethylbenzimidazole Under Green Conditions
Corresponding Author(s) : S. Srinivas Rao
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
A green approach for the synthesis of 1-alkyl-2-chloromethylbenzimidazoles (3) (R1 = CH3, C2H5, CH2Ph) under, different conditions has been developed from 2-chloromethylbenzimidazole (2) by reaction with an alkylating agent (i.e. DMS, DES, PhCH2Cl) by physical grinding or by using green solvent like PEG-600 or by using micro-wave irradiation technique.
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- (a) G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); doi:10.1021/jm00051a010; (b) J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu and E.J. LaVoie, Eur. J. Med. Chem., 39, 992 (1996); doi:10.1021/jm950412w; (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); doi:10.1021/jm970096g; (d) D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); doi:10.1021/cr020033s.
- (a) G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); doi:10.1021/jm00051a010; (b) B. Jayashankara, ARKIVOC, 75 (2008); doi:10.3998/ark.5550190.0009.b07; (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); doi:10.1021/jm970096g.
- H. Hasegawa, N. Tsuda and M. Hasoya, Japanese Patent, 72,55,198 (1974); Chem. Abstr., 156308 (1975).
- G. Rovnyak, V.L. Narayana, R.D. Haugwitz and C.M. Cimarusti, US Patent, 3,927,014 (1975); Chem. Abstr., 84, 105596m (1975).
- S.C. Bell and P.H. Wei, J. Med. Chem., 19, 524 (1976); doi:10.1021/jm00226a016.
- D.R. Graber, R.A. Morge and J.C. Sih, J. Org. Chem., 52, 4620 (1987); doi:10.1021/jo00229a039.
- N.I. Korotkikh, G.F. Raenko and O.P. Shvaika, Chem. Heterocycl. Comp., 31, 359 (1995); doi:10.1007/BF01373558.
- N.I. Korotkikh, A.F. Aslanov and G.F. Raenko, Russ. J. Org. Chem., 31, 721 (1995); Chem. Abstr., 18833 (1997).
- R.K. Verma, R. Mall, P. Ghosh and V. Kumar, Syn. Comm., 43, 1882 (2013); doi:10.1080/00397911.2012.678461.
- W.J. Flosi, D.A. DeGoey, D.J. Grampovnik, H. Chen, L.L. Klein, T. Dekhtyar, S. Masse, K.C. Marsh, H.M. Mo and D. Kempf, Bioorg. Med. Chem., 14, 6695 (2006); doi:10.1016/j.bmc.2006.05.063.
- P.K. Kumar and P.K. Dubey, Asian J. Chem., 24, 3249 (2012).
- S.S. Rao, P.K. Dubey and Y.B. Kumari, Indian J. Chem., 52B, 1210 (2013).
References
(a) G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); doi:10.1021/jm00051a010; (b) J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu and E.J. LaVoie, Eur. J. Med. Chem., 39, 992 (1996); doi:10.1021/jm950412w; (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); doi:10.1021/jm970096g; (d) D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); doi:10.1021/cr020033s.
(a) G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); doi:10.1021/jm00051a010; (b) B. Jayashankara, ARKIVOC, 75 (2008); doi:10.3998/ark.5550190.0009.b07; (c) T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); doi:10.1021/jm970096g.
H. Hasegawa, N. Tsuda and M. Hasoya, Japanese Patent, 72,55,198 (1974); Chem. Abstr., 156308 (1975).
G. Rovnyak, V.L. Narayana, R.D. Haugwitz and C.M. Cimarusti, US Patent, 3,927,014 (1975); Chem. Abstr., 84, 105596m (1975).
S.C. Bell and P.H. Wei, J. Med. Chem., 19, 524 (1976); doi:10.1021/jm00226a016.
D.R. Graber, R.A. Morge and J.C. Sih, J. Org. Chem., 52, 4620 (1987); doi:10.1021/jo00229a039.
N.I. Korotkikh, G.F. Raenko and O.P. Shvaika, Chem. Heterocycl. Comp., 31, 359 (1995); doi:10.1007/BF01373558.
N.I. Korotkikh, A.F. Aslanov and G.F. Raenko, Russ. J. Org. Chem., 31, 721 (1995); Chem. Abstr., 18833 (1997).
R.K. Verma, R. Mall, P. Ghosh and V. Kumar, Syn. Comm., 43, 1882 (2013); doi:10.1080/00397911.2012.678461.
W.J. Flosi, D.A. DeGoey, D.J. Grampovnik, H. Chen, L.L. Klein, T. Dekhtyar, S. Masse, K.C. Marsh, H.M. Mo and D. Kempf, Bioorg. Med. Chem., 14, 6695 (2006); doi:10.1016/j.bmc.2006.05.063.
P.K. Kumar and P.K. Dubey, Asian J. Chem., 24, 3249 (2012).
S.S. Rao, P.K. Dubey and Y.B. Kumari, Indian J. Chem., 52B, 1210 (2013).