Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles

Arumugam, Natarajan and Abdul Rahim, Aisyah Saad and Abd Hamid, Shafida and Osman, Hasnah (2012) Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles. Molecules , 17 (8). pp. 9887-9899. ISSN 1420-3049

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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.

Item Type:	Article (Journal)
Additional Information:	5980/29253
Uncontrolled Keywords:	2-arylbenzimidazole; microwave-assisted synthesis; α-glycoside; glycosylation; glycomimetic
Subjects:	Q Science > Q Science (General)
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science
Depositing User:	Nur' Aini Abu Bakar
Date Deposited:	01 Mar 2013 09:22
Last Modified:	19 Aug 2016 15:47
URI:	http://irep.iium.edu.my/id/eprint/29253

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