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Synthesis and Characterization of ortho-Xylyl Linked Bis-benzimidazolium Salts (Part-II)
Corresponding Author(s) : Rosenani A. Haque
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
A number of N-alkylbenzimidazoles were synthesized by reactions of benzimidazole with alkyl halides (PentBr, HexBr, OctBr, DecBr). The subsequent treatment of the resulting N-alkylbenzimidazoles with 1,2-bis(bromomethylene) benzene afforded corresponding bis-benzimidazolium salts. All the compounds were characterized by spectroscopic techniques (NMR and FT-IR) and microanalysis. Molecular structures of selected compounds were established through single crystal X-ray diffraction studies.
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- W.A. Herrmann, Angew. Chem. Int. Ed., 47, 1290 (2002).
- A. Kascatan-Nebioglu, M.J. Panzner, C.A. Tessier, C.L. Cannon, W.J. Youngs, Coord. Chem. Rev., 251, 884 (2007).
- B. Ruan, Y. Tian, H. Zhou, J. Wu, Z. Liu, C. Zhu, J. Yang and H. Zhu, J. Organomet. Chem., 694, 2883 (2009).
- P.J. Barnard, M.V. Baker, S.J. Berners-Price and D.A. Day, J. Inorg. Biochem., 98, 1642 (2004).
- M.-L. Teyssot, A.-S. Jarrousse, M. Manin,A. Chevry, S. Roche, F. Norre, C. Beaudoin, L. Morel, D. Boyer, R. Mahiou and A. Gautier, Dalton Trans., 6894 (2009).
- O.H. Winkelmann and O. Navarro, Adv. Synth. Catal., 352, 212 (2010).
- W.A. Herrmann, M. Elison, J. Fischer, C. Köcher and G.R.J. Artus, Angew. Chem. Int. Ed., 34, 2371 (1995).
- J. Cheng and M.L. Trudell, Org. Lett., 3, 1371 (2001).
- S. Lee and J.F. Hartwig, J. Org. Chem., 66, 3402 (2001).
- W.A. Herrmann, L.J. Goossen, C. Köcher, G.R.J. Artus, Angew. Chem. Int. Ed. English, 35, 2805 (1996).
- T. Weskamp, W.C. Schattenmann, M. Spiegler and W.A. Herrmann, Angew. Chem. Int. Ed., 37, 2490 (1998).
- T.-L. Choi, A.K. Chatterjee and R.H. Grubbs, Angew. Chem. Int. Ed., 40, 1277 (2001).
- R.A. Haque and M.A. Iqbal, Asian J. Chem., 24, 2625 (2012).
- R.A. Haque, M.A. Iqbal, M. Hemamalini,; H.-K. Fun, Acta Crystallogr. Sect. E, 67, o1814 (2011).
- O.V. Starikova, G.V. Dolgushin, L.I. Larina, P.E. Ushakov, T.N. Komarova and T.N. Lopyrev, Russ. J. Org. Chem., 39, 1467 (2003).
- B. Dariusz, J. Pielichowski and K. Jaskot, Heterocycles, 45, 715 (1997).
- R.A. Haque, Metal Complexes of N-Heterocyclic Carbene; Silver, Mercury, Ruthenium and Palladium Complexes of N-Heterocyclic Carbene-Linked Cyclophane: Synthesis, Molecular Structures and Characterization, Verlag Dr. Muller, edn. 1, Vol. 1 (2009).
- M.A. Iqbal, R.A. Haque, S. Shukri and T. Izzati, J. Chem., 2, 17 (2011).
- M. Hranjec, K. Starcevic, S.K. Pavelic, P. Lucin, K. Pavelic and Z.G. Karminski, Eur. J. Med. Chem., 46, 2274 (2011).
- S.A. Galal, K.H. Hegab, A.S. Kassab, M.L. Rodriguez, S.M. Kerwin, A.-M. El-Khamry and H.I. El Diwani, Eur. J. Med. Chem., 44, 1500 (2009).
- M.A. Iqbal, R.A. Haque, H.-K. Fun and T.S. Chia, Acta Crystallogr., E68 (2012) in Press.
- R.A. Haque, M.A. Iqbal, H.-Fun and S. Arshad, Acta Crystallogr., E68, o924 (2012).
References
W.A. Herrmann, Angew. Chem. Int. Ed., 47, 1290 (2002).
A. Kascatan-Nebioglu, M.J. Panzner, C.A. Tessier, C.L. Cannon, W.J. Youngs, Coord. Chem. Rev., 251, 884 (2007).
B. Ruan, Y. Tian, H. Zhou, J. Wu, Z. Liu, C. Zhu, J. Yang and H. Zhu, J. Organomet. Chem., 694, 2883 (2009).
P.J. Barnard, M.V. Baker, S.J. Berners-Price and D.A. Day, J. Inorg. Biochem., 98, 1642 (2004).
M.-L. Teyssot, A.-S. Jarrousse, M. Manin,A. Chevry, S. Roche, F. Norre, C. Beaudoin, L. Morel, D. Boyer, R. Mahiou and A. Gautier, Dalton Trans., 6894 (2009).
O.H. Winkelmann and O. Navarro, Adv. Synth. Catal., 352, 212 (2010).
W.A. Herrmann, M. Elison, J. Fischer, C. Köcher and G.R.J. Artus, Angew. Chem. Int. Ed., 34, 2371 (1995).
J. Cheng and M.L. Trudell, Org. Lett., 3, 1371 (2001).
S. Lee and J.F. Hartwig, J. Org. Chem., 66, 3402 (2001).
W.A. Herrmann, L.J. Goossen, C. Köcher, G.R.J. Artus, Angew. Chem. Int. Ed. English, 35, 2805 (1996).
T. Weskamp, W.C. Schattenmann, M. Spiegler and W.A. Herrmann, Angew. Chem. Int. Ed., 37, 2490 (1998).
T.-L. Choi, A.K. Chatterjee and R.H. Grubbs, Angew. Chem. Int. Ed., 40, 1277 (2001).
R.A. Haque and M.A. Iqbal, Asian J. Chem., 24, 2625 (2012).
R.A. Haque, M.A. Iqbal, M. Hemamalini,; H.-K. Fun, Acta Crystallogr. Sect. E, 67, o1814 (2011).
O.V. Starikova, G.V. Dolgushin, L.I. Larina, P.E. Ushakov, T.N. Komarova and T.N. Lopyrev, Russ. J. Org. Chem., 39, 1467 (2003).
B. Dariusz, J. Pielichowski and K. Jaskot, Heterocycles, 45, 715 (1997).
R.A. Haque, Metal Complexes of N-Heterocyclic Carbene; Silver, Mercury, Ruthenium and Palladium Complexes of N-Heterocyclic Carbene-Linked Cyclophane: Synthesis, Molecular Structures and Characterization, Verlag Dr. Muller, edn. 1, Vol. 1 (2009).
M.A. Iqbal, R.A. Haque, S. Shukri and T. Izzati, J. Chem., 2, 17 (2011).
M. Hranjec, K. Starcevic, S.K. Pavelic, P. Lucin, K. Pavelic and Z.G. Karminski, Eur. J. Med. Chem., 46, 2274 (2011).
S.A. Galal, K.H. Hegab, A.S. Kassab, M.L. Rodriguez, S.M. Kerwin, A.-M. El-Khamry and H.I. El Diwani, Eur. J. Med. Chem., 44, 1500 (2009).
M.A. Iqbal, R.A. Haque, H.-K. Fun and T.S. Chia, Acta Crystallogr., E68 (2012) in Press.
R.A. Haque, M.A. Iqbal, H.-Fun and S. Arshad, Acta Crystallogr., E68, o924 (2012).