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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| Format: | Article |
| Language: | English |
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MDPI
2012
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| Online Access: | 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 |
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| 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 |
| building | IIUM Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-14T15:28:07Z |
| format | Article |
| id | iium-29253 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T15:28:07Z |
| publishDate | 2012 |
| publisher | MDPI |
| recordtype | eprints |
| repository_type | Digital Repository |
| 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. |
| 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 |
| title | 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_short | 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 |
| topic | Q Science (General) |
| 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 |