Parallel synthesis of 2-sulphanylated bis-benzimidazoles on soluble polymer support.
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.
Chang
Chia-Mao
CM
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300-10, Taiwan, ROC.
Kulkarni
Manohar V
MV
Chen
Chih-Hau
CH
Wang
Chi-Hsiang
CH
Sun
Chung-Ming
CM
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
D000577:Amides; D001562:Benzimidazoles; D013438:Sulfhydryl Compounds; D011092:Polyethylene Glycols