Next Article in Journal
Formation of Aldehyde and Ketone Compounds during Production and Storage of Milk Powder
Previous Article in Journal
Synthesis and Bioactivity Evaluation of New 6-Aryl-5-cyano Thiouracils as Potential Antimicrobial and Anticancer Agents
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
Received: 27 June 2012; in revised form: 27 July 2012 / Accepted: 13 August 2012 / Published: 17 August 2012
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [324 KB, updated 18 June 2014; original version uploaded 18 June 2014]   |   Browse Figures
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.

Export to BibTeX |
EndNote


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.

AMA Style

Arumugam N, Abdul Rahim AS, Abd Hamid S, Osman H. Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles. Molecules. 2012; 17(8):9887-9899.

Chicago/Turabian Style

Arumugam, Natarajan; Abdul Rahim, Aisyah Saad; Abd Hamid, Shafida; Osman, Hasnah. 2012. "Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles." Molecules 17, no. 8: 9887-9899.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert