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

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

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...

Full description

Bibliographic Details
Main Authors: Arumugam, Natarajan, Abdul Rahim, Aisyah Saad, Abd Hamid, Shafida, Osman, Hasnah
Format: Article
Language:English
Published: MDPI 2012
Subjects:
Q Science (General)
Online Access:http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/1/Straightforward_Synthesis_of_Novel_1-%282%E2%80%B2-%CE%B1-O-D-Glucopyranosyl.pdf
id iium-29253
recordtype eprints
spelling iium-292532016-08-19T07:47:08Z http://irep.iium.edu.my/29253/ Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles Arumugam, Natarajan Abdul Rahim, Aisyah Saad Abd Hamid, Shafida Osman, Hasnah Q Science (General) 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. MDPI 2012-08 Article PeerReviewed application/pdf en http://irep.iium.edu.my/29253/1/Straightforward_Synthesis_of_Novel_1-%282%E2%80%B2-%CE%B1-O-D-Glucopyranosyl.pdf 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 http://www.mdpi.com/1420-3049/17/8/9887 10.3390/molecules17089887.
repository_type Digital Repository
institution_category Local University
institution International Islamic University Malaysia
building IIUM Repository
collection Online Access
language English
topic Q Science (General)
spellingShingle Q Science (General)
Arumugam, Natarajan
Abdul Rahim, Aisyah Saad
Abd Hamid, Shafida
Osman, Hasnah
Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
description 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.
format Article
author Arumugam, Natarajan
Abdul Rahim, Aisyah Saad
Abd Hamid, Shafida
Osman, Hasnah
author_facet Arumugam, Natarajan
Abdul Rahim, Aisyah Saad
Abd Hamid, Shafida
Osman, Hasnah
author_sort Arumugam, Natarajan
title Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
title_short Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
title_full Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
title_fullStr Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
title_full_unstemmed Straightforward synthesis of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles
title_sort straightforward synthesis of novel 1-(2'-α-o-d-glucopyranosyl ethyl) 2-arylbenzimidazoles
publisher MDPI
publishDate 2012
url http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/
http://irep.iium.edu.my/29253/1/Straightforward_Synthesis_of_Novel_1-%282%E2%80%B2-%CE%B1-O-D-Glucopyranosyl.pdf
first_indexed 2023-09-18T20:42:55Z
last_indexed 2023-09-18T20:42:55Z
_version_ 1777409485114966016

Similar Items