An efficient one-pot synthesis of novel ethyl 2-((1H-benzo[d]imidazol-2- ylamino)(aryl)methylthio) acetates using Ni(NO3)2.6H2O, as a homogeneous catalyst

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 39, Issue 9, 2009, Pages 509-511

  Mobinikhaledi, Akbar ^a   Foroughifar, Naser ^a   Kalhor, Mehdi ^a  

^a ARAK UNIVERSITY   (Iran)

Author keywords

2 Amino benzimidazole; Catalyst; One pot reaction

Indexed keywords

EID: 71049178624     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533170903324585     Document Type: Article

References (20)

1. Ugi, I., Dömling, A., and Hörl, W. Multicomponent reactions in organic chemistry. Endeavour 1994, 18, 115-122.
2. Tietze, L.F. Domino reactions in organic synthesis. Chem. Rev., 1996, 96, 115-136.
3. Balme, G., Bossharth, E., and Monteiro, N. Pd-Assisted multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 2003, 4101-4111.
4. Zhu, J., and Bienayme, H. Multicomponent Reactions, 2005, Wiley-VCH, Weinheim
5. For a special issue on MCRs, see Tetrahedron 2005, 61, 11299.
6. Menendez, J. C. Multicomponent reactions. Synthesis 2006, 2624-2624
7. Plunkett, M., and Ellman, J.A. Combinatorial chemistry and new drugs. Sci. Am., 1997, 276, 68-73.
8. Tietze, L. F. and Modi, A. Multicomponent domino reactions for the synthesis of biologically active natural products and drugs. Med. Res. Rev., 2000, 20, 304-322.
9. Weber, L. Multicomponent reactions and evolutionary chemistry. Drug Discovery Today 2002, 7, 143-147.
10. Roth, T., Morningstar, M.L., Boyer, P.L., Hughes, S.H.; Buckheit Jr., R.W., and Michejda, C.J. Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase: 2-aryl-substituted benzimidazoles. J. Med. Chem., 1997, 40, 4199-4207.
11. Kazimierczuk, Z., and Shugar, D. Preparation and properties of the 5,6- and 4,6(5,7)-dinitro derivatives of benzimidazole and their 1-β- Dribofuranosides. Nucleosides Nucleotides 1989, 8, 1379-1385.
12. Andrzejewska, M., Mulia, L.Y., Rivera, R.C., Tapia, A., Vilpo, L., and Kazimiereczuk, Z. Synthesis, antiprotozoal and anticancer activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles. Eur. J. Med. Chem., 2002, 37, 973-978.
13. Beaulieu, P.L., Bös, M., Bousquet, Y., Fazal, G., Gauthier, J., Gillard, J., Goulet, S., LaPlante, S., Poupart, M.A., Lefebvre, S., McKerche, G., Pellerin, C., Austel, V., and Kukolj, G. Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase: Discovery and preliminary SAR of benzimidazole derivatives. Bioorg. Med. Chem. Lett., 2004, 14, 119-124. (Pubitemid 38016210)
14. Ramla, M.M., Omar, A.M., Tokudo, H., and El-Diwoni, I.H. Synthesis and inhibitory activity of new benzimidazole derivatives against Burkitt's lymphoma promotion. Bioorg. Med. Chem., 2007, 15, 6489-6496.
15. Göker, H., Özden, S., Yildiz, S., and Boykin, D.W. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubsti-tuted-1Hbenzimidazole- N-alkylated-5-carboxamidines. Eur. J. Med. Chem., 2005, 40, 1062-1069.
16. Clemons, G.P., and Sisler, H.D. Localization of the site of action of a fungitoxic benomyl derivative. Pestic. Biochem. Physiol., 1971, 1, 32-43.
17. Mobinikhaledi, A., and Steel, P.J. Synthesis of perimidines using copper nitrate as an efficient catalyst. Syn. Reac. Inorg. Met-org. Chem., 2009, 39, 133-135.
18. Mobinikhaledi, A., Steel, P.J., and Palson M. Rapid and efficient synthesis of Schiff bases catalyzed by copper nitrate. Syn. Reac. Inorg. Met-org. Chem., 2009, 39, 189-192.
19. Mobinikhaledi, A., Foroughifar, N., Bodaghi Fard, M.A.; Moghanian, H., Ebrahimi, S., andKalhor,M. Efficient one-pot synthesis of polyhydroquinoline derivatives using silica sulfuric acid as a heterogeneous and reusable catalyst under conventional heating and energy-saving microwave irradiation. Synth. Commun., 2009, 39, 1166-1174.
20. Foroughifar, N., Mobinikhaledi, Bodaghi Farad, M.A., Moghanian, H., and Ebrahimi, S. Sulfamic acid catalyzed one-pot synthesis of polyhydroquinolines via the Hantzsch four component condensation reaction Syn. Reac. Inorg. Met-org. Chem., 2009, 39, 161-164.