title: Parallel synthesis of 2-sulphanylated bis-benzimidazoles on soluble polymer support.
abstract: A well-sustained multistep synthetic protocol has been designed for the PEG-functionalized aromatic acid amide to generate a molecular library of 2-alkylthio bis-benzimidazoles. An attempted synthesis of benzimidazole-2-thiol in dichloromethane has led to S-chloromethyl methyl sulfides, mimicking bacterial enzymatic systems. Regioselective S-alkylation was brought about under controlled conditions using a mild base at room temperature. The polymer-free compounds, 2-sulfanylated bisbenzimidazoles, were obtained in high yields and high purities. Chemical shift changes in proton and carbon NMR have been employed to monitor the progress of the reaction steps and to prove the site of S-alkylation, respectively.
authors.affiliation: Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan, ROC.
authors.forename: Chia-Mao
authors.initials: CM
authors.lastname: Chang
authors.forename: Manohar V
authors.initials: MV
authors.lastname: Kulkarni
authors.forename: Chih-Hau
authors.initials: CH
authors.lastname: Chen
authors.forename: Chi-Hsiang
authors.initials: CH
authors.lastname: Wang
authors.forename: Chung-Ming
authors.initials: CM
authors.lastname: Sun
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D011092:Polyethylene Glycols / Q000737:chemistry*; D012015:Reference Standards; D012995:Solubility; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D001562:Benzimidazoles; D013438:Sulfhydryl Compounds; D011092:Polyethylene Glycols