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

ABSTRACT: A series of novel 1-(2'-?-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'-?-O-D-glucopyranosyl ethyl) 2-aryl-benzimidazoles in a simple and straightforward manner.

SUBMITTER: Arumugam N

PROVIDER: S-EPMC6268058 | biostudies-literature | 2012 Aug

REPOSITORIES: biostudies-literature

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

Arumugam Natarajan N Abdul Rahim Aisyah Saad AS Abd Hamid Shafida S Osman Hasnah H

Molecules (Basel, Switzerland) 20120817 8

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 ...[more]

PMID: 22902883

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