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Molecules 2012, 17(8), 9887-9899; doi:10.3390/molecules17089887
Article

Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles

1,†, 1,* , 2 and 3
1 School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia 2 Kulliyyah of Science, International Islamic University Malaysia (IIUM), Jalan Istana, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia 3 School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia Current address: Department of Chemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi Arabia.
* Author to whom correspondence should be addressed.
Received: 27 June 2012 / Revised: 27 July 2012 / Accepted: 13 August 2012 / Published: 17 August 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

A series of novel 1-(2′-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles has been prepared via one-pot glycosylation of ethyl-1-(2'-hydroxyethyl)-2-arylbenzimidazole-5-carboxylate derivatives. Synthesis of the 2-arylbenzimidazole aglycones from 4-fluoro-3-nitrobenzoic acid was accomplished in four high-yielding steps. The reduction and cyclocondensation steps for the aglycone synthesis proceeded efficiently under microwave irradiation to afford the appropriate benzimidazoles in excellent yields within 2–3 min. Glycosylation of the hydroxyethyl aglycones with the perbenzylated 1-hydroxy- glucopyranose, pretreated with the Appel-Lee reagent, followed by catalytic hydrogenolysis delivered the desired 1-(2′-α-O-D-glucopyranosyl ethyl) 2-aryl-benzimidazoles in a simple and straightforward manner.
Keywords: 2-arylbenzimidazole; microwave-assisted synthesis; α-glycoside; glycosylation; glycomimetic 2-arylbenzimidazole; microwave-assisted synthesis; α-glycoside; glycosylation; glycomimetic
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Arumugam, N.; Abdul Rahim, A.S.; Abd Hamid, S.; Osman, H. Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles. Molecules 2012, 17, 9887-9899.

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