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

• 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/29253/1/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
• Institution: Universiti Islam Antarabangsa Malaysia

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.