119th General Meeting of the KCS

Type Poster Presentation
Area 의약화학
Room No. 포스터발표장
Time 4월 20일 (목요일) 11:00~12:30
Code MEDI.P-426
Subject Synthesis of 1-alkyl-N-alkyl/acyl-1H-benzo[d]imidazole-2-amine derivatives via desulfurative cyclization on solid-phase organic synthesis
Authors 유현정, 권혜진, 공영대*
동국대학교 화학과, Korea
Abstract In this study, we synthesized 1-alkyl-N-alkyl/acyl-1H-benzo[d]imidazole-2-amine derivatives. 2-Fluoronitro benzene was used as a starting material and reacted with various amines. With the N-alkyl-2-nitroanilines in hand, N1-alkylbenzene-1,2-diamines were obtained through a reduction reaction. Next, N1-alkylbenzene-1,2-diamines reacted with polymer supported isothiocyanate derived from 4-benzyloxy-2-methoxybenzylamine (BOMBA) resin through a reaction with carbondisulfide, trimethylamine p-TsCl in tetrahydrofuran to generate thiourea intermediate resin. The cyclization of thiourea intermediate resin was successfully conducted through desulfurative cyclization with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and N,N-diisopropylethylamine in dichloromethane (DCM). Next, various electrophiles such as alkyl halide, acid chlorides were introduced at 2-amine position. Finally, we obtained various 1-alkyl-N-alkyl/acyl-1H-benzo[d]imidazole-2-amine by cleavage of the corresponding resin under trifluoroacetic acid (TFA) in dichloromethane (DCM).
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