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A Green Approach for the Synthesis of 1-Methyl-2-(alkylthio)-1H-benzimidazoles
Corresponding Author(s) : S. Srinivas Rao
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
A green approach for the synthesis of 1-methyl-2-(alkylthio)-1H-benzimidazoles 6 (R1 = CH3, C2H5, CH2Ph) under, different conditions has been developed from N-methyl-2-mercaptobenzimidazole (i.e. CH3) 5 by reaction with an alkylating agent 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, 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. Jayasankara and K.M.L. Rai, ARKIVOC, 75, (2008); (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 198 (1974); Chem. Abstr., 156308 (1975).
- G. Rovnyak, V.L. Narayana, R.D. Haugwitz and C.M. Cimarusti, US Patent 1973014; Chem. Abstr., 105596 (1974).
- 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).
- T.R. Lee and K. Kim, J. Heterocycl. Chem., 26, 747 (1989); doi:10.1002/jhet.5570260344.
- B. Stanovnik, M. Tisler, A. Hribar, G.B. Barlin and D.J. Brown, Aust. J. Chem., 34, 1729 (1981); doi:10.1071/CH9811729.
- P.K. Dubey, A. Naidu and P.V.V. Reddy, Indian J. Chem., 47B, 1443 (2008).
- 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, 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. Jayasankara and K.M.L. Rai, ARKIVOC, 75, (2008); (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 198 (1974); Chem. Abstr., 156308 (1975).
G. Rovnyak, V.L. Narayana, R.D. Haugwitz and C.M. Cimarusti, US Patent 1973014; Chem. Abstr., 105596 (1974).
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).
T.R. Lee and K. Kim, J. Heterocycl. Chem., 26, 747 (1989); doi:10.1002/jhet.5570260344.
B. Stanovnik, M. Tisler, A. Hribar, G.B. Barlin and D.J. Brown, Aust. J. Chem., 34, 1729 (1981); doi:10.1071/CH9811729.
P.K. Dubey, A. Naidu and P.V.V. Reddy, Indian J. Chem., 47B, 1443 (2008).
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).