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Syntheses of Biologically Active Bisbenzimidazolylesulphone Derivatives
Corresponding Author(s) : Sadhu Srinivas Rao
Asian Journal of Chemistry,
Vol. 29 No. 8 (2017): Vol 29 Issue 8
Abstract
2-(1-Chloroethyl)-1H-benzimidazole on condensation with 2-mercaptobenzimidazole in methanol using triethylamine as a base under reflux for 3 h yielded 2-((1-(1H-benzimidazol-2-yl)ethyl)thio)-1H-benzimidazole which on alkylation using two equivalent of alkylating agent under phase transfer catalyst conditions give N,N’-dialkylbisbenzimidazole sulphides. Upon oxidation with H2O2 in acetic acid under reflux for 2 h gave N,N’-dialkylbisbenzimidazole sulphones which are analogues of prazoles.
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- C.M. Adams, I. Ghosh and Y. Kishi, Org. Lett., 6, 4723 (2004); https://doi.org/10.1021/ol048059o.
- N. Neamati, A. Mazumder, R.J. Schultz and Y. Pommier, Antimicrob. Agents Chemother., 41, 385 (1997).
- T.M. Williams, T.M. Ciccarone, S.C. MacTough, C.S. Rooney, S.K. Balani, J.H. Condra, E.A. Emini, M.E. Goldman and W.J. Greenlee, J. Med. Chem., 36, 1291 (1993); https://doi.org/10.1021/jm00061a022.
- S. Répichet, C. Le Roux, P. Hernandez, J. Dubac and J.-R. Desmurs, J. Org. Chem., 64, 6479 (1999); https://doi.org/10.1021/jo9902603.
- A. Kar, I.A. Sayyed, W.F. Lo, H.M. Kaiser, M. Beller and M.K. Tse, Org. Lett., 9, 3405 (2007); https://doi.org/10.1021/ol071396n.
- F.R. Jensen and B. Goldman, in ed.: G.A. Olah, Friedel- Crafts and Related Reactions, vol. 3, pp. 1319 (1964).
- M.V. Alexander, A.C. Khandekar and S.D. Samant, J. Mol. Catal. Chem., 223, 75 (2004); https://doi.org/10.1016/j.molcata.2003.10.066.
- E. Bouman, W.L. Driessen and J. Reedijk, Coord. Chem. Rev., 104, 143 (1990); https://doi.org/10.1016/0010-8545(90)80042-R.
- E.S. Lane, J. Chem. Soc., 534 (1955); https://doi.org/10.1039/jr9550000534.
- E. Dall’Oglio, M.B. Caro, J.C. Gesser, C. Zucco and M.C. Rezende, J. Braz. Chem. Soc., 13, 251 (2002); https://doi.org/10.1590/S0103-50532002000200018.
- A.S. Alpan, G. Zencir, I. Zupkó, G. Coban, B. Réthy, H.S. Gunes and Z. Topcu, J. Enzyme Inhib. Med. Chem., 24, 844 (2009); https://doi.org/10.1080/14756360802420831.
- S.S. Rao and P.K. Dubey, Indian J. Chem., 54B, 698 (2015).
References
C.M. Adams, I. Ghosh and Y. Kishi, Org. Lett., 6, 4723 (2004); https://doi.org/10.1021/ol048059o.
N. Neamati, A. Mazumder, R.J. Schultz and Y. Pommier, Antimicrob. Agents Chemother., 41, 385 (1997).
T.M. Williams, T.M. Ciccarone, S.C. MacTough, C.S. Rooney, S.K. Balani, J.H. Condra, E.A. Emini, M.E. Goldman and W.J. Greenlee, J. Med. Chem., 36, 1291 (1993); https://doi.org/10.1021/jm00061a022.
S. Répichet, C. Le Roux, P. Hernandez, J. Dubac and J.-R. Desmurs, J. Org. Chem., 64, 6479 (1999); https://doi.org/10.1021/jo9902603.
A. Kar, I.A. Sayyed, W.F. Lo, H.M. Kaiser, M. Beller and M.K. Tse, Org. Lett., 9, 3405 (2007); https://doi.org/10.1021/ol071396n.
F.R. Jensen and B. Goldman, in ed.: G.A. Olah, Friedel- Crafts and Related Reactions, vol. 3, pp. 1319 (1964).
M.V. Alexander, A.C. Khandekar and S.D. Samant, J. Mol. Catal. Chem., 223, 75 (2004); https://doi.org/10.1016/j.molcata.2003.10.066.
E. Bouman, W.L. Driessen and J. Reedijk, Coord. Chem. Rev., 104, 143 (1990); https://doi.org/10.1016/0010-8545(90)80042-R.
E.S. Lane, J. Chem. Soc., 534 (1955); https://doi.org/10.1039/jr9550000534.
E. Dall’Oglio, M.B. Caro, J.C. Gesser, C. Zucco and M.C. Rezende, J. Braz. Chem. Soc., 13, 251 (2002); https://doi.org/10.1590/S0103-50532002000200018.
A.S. Alpan, G. Zencir, I. Zupkó, G. Coban, B. Réthy, H.S. Gunes and Z. Topcu, J. Enzyme Inhib. Med. Chem., 24, 844 (2009); https://doi.org/10.1080/14756360802420831.
S.S. Rao and P.K. Dubey, Indian J. Chem., 54B, 698 (2015).