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...
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my.iium.irep.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 REM 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. |
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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 |
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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 |
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MDPI |
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2012 |
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http://irep.iium.edu.my/29253/1/Straightforward_Synthesis_of_Novel_1-%282%E2%80%B2-%CE%B1-O-D-Glucopyranosyl.pdf http://irep.iium.edu.my/29253/ http://www.mdpi.com/1420-3049/17/8/9887 |
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13.18916 |