A one-pot tandem synthesis of various 1,2-disubstituted benzimidazoles
作者： Keng Yoon Yeong , Mohamed Ashraf Ali , Chee Wei Ang , Soo Choon Tan , Hasnah Osman
DOI: 10.1016/J.TETLET.2014.07.008
关键词:
摘要: A facile method to synthesize various 1,2-disubstituted benzimidazoles is developed. It suggested that formation of a Meisenheimer adduct between the substrate, amine, and solvent aids N-arylation process. The generality protocol demonstrated by efficient reactions involving numerous substituents ranging from electron-withdrawing groups electron-donating groups.
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Canan Kuş, Synthesis of New Substituted 6-(morpholin-4-yl)-1H-Benzimidazole Derivatives Turkish Journal of Chemistry. ,vol. 26, pp. 559- 564 ,(2002)
Jerry March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure ,(1977)
Lucinda M. Dudd, Eleni Venardou, Eduardo Garcia-Verdugo, Peter Licence, Alexander J. Blake, Claire Wilson, Martyn Poliakoff, Synthesis of benzimidazoles in high-temperature water Green Chemistry. ,vol. 5, pp. 187- 192 ,(2003) , 10.1039/B212394K
Jorge Alonso, Nis Halland, Marc Nazaré, Omar R'kyek, Matthias Urmann, Andreas Lindenschmidt, A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines European Journal of Organic Chemistry. ,vol. 2011, pp. 234- 237 ,(2011) , 10.1002/EJOC.201001423
Meihua Shen, Tom G. Driver, Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides. Organic Letters. ,vol. 10, pp. 3367- 3370 ,(2008) , 10.1021/OL801227F
Hassan Zali Boeini, Khadijeh Hajibabaei Najafabadi, Efficient One‐Step Synthesis of Benzazoles in Aqueous Media European Journal of Organic Chemistry. ,vol. 2009, pp. 4926- 4929 ,(2009) , 10.1002/EJOC.200900740
Damodara N. Kommi, Pradeep S. Jadhavar, Dinesh Kumar, Asit K. Chakraborti, “All-water” one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: hydrogen bond driven ‘synergistic electrophile–nucleophile dual activation’ by water Green Chemistry. ,vol. 15, pp. 798- 810 ,(2013) , 10.1039/C3GC37004F
Johannes Schwöbel, Ralf-Uwe Ebert, Ralph Kühne, Gerrit Schüürmann, Prediction of the intrinsic hydrogen bond acceptor strength of chemical substances from molecular structure. Journal of Physical Chemistry A. ,vol. 113, pp. 10104- 10112 ,(2009) , 10.1021/JP904812B
Yeong Keng Yoon, Mohamed Ashraf Ali, Ang Chee Wei, Tan Soo Choon, Kooi-Yeong Khaw, Vikneswaran Murugaiyah, Hasnah Osman, Vijay H Masand, Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors. Bioorganic Chemistry. ,vol. 49, pp. 33- 39 ,(2013) , 10.1016/J.BIOORG.2013.06.008
Prasenjit Saha, Md Ashif Ali, Pokhraj Ghosh, Tharmalingam Punniyamurthy, None, Cobalt-catalyzed intramolecular C–N and C–O cross-coupling reactions: synthesis of benzimidazoles and benzoxazoles Organic and Biomolecular Chemistry. ,vol. 8, pp. 5692- 5699 ,(2010) , 10.1039/C0OB00405G