120th General Meeting of the KCS

Type Poster Presentation
Area Medicinal Chemistry
Room No. Exhibition Hall 2+3
Time 10월 19일 (목요일) 11:00~12:30
Code MEDI.P-301
Subject Synthesis of 1-Alkyl- 2-amido-Benzo[d]imidazoles on Solid-phase via Desulfurative Cyclization of Thiourea Resin
Authors HYUNJEONG YOO, seung ju yang, Young Dae Gong*
Department of Chemistry, Dongguk University, Korea
Abstract In this study, we synthesized 1-Alkyl- 2-amido-Benzo[d]imidazoles derivatives. Substituted N1-alkylbenzene-1,2-diamines reacted with polymer supported isothiocyanate resin derived from 4-benzyloxy-2-methoxybenzylamine (BOMBA) resin through a reaction with carbon disulfide, trimethylamine and p-TsCl in tetrahydrofuran to generate thiourea intermediate resin. The desulfurative cyclization of thiourea intermediate resin was successfully conducted with using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and N,N-diisopropylethylamine in dichloromethane (DCM) to afford 2-amino-Benzo[d]imidazoles resin, and then diverse acid chlorides were introduced at 2-amine position. In case of 3-nitrobenzoyl chloride, nitro group was reduced by Tin(Ⅱ) chloride in DMF followed by reaction with amino acids and aldehydes for further diversification. Finally, we obtained various 1-Alkyl- 2-amido-Benzo[d]imidazoles by cleavage of the corresponding resin under trifluoroacetic acid (TFA) in dichloromethane (DCM).
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