Combinatorial liquid-phase synthesis of structurally diverse benzimidazole libraries

被引：62

作者：

Yeh, CM ^{[1
]}

Tung, CL ^{[1
]}

Sun, CM ^{[1
]}

机构：

[1] Natl Dong Hwa Univ, Dept Chem, Hualien 974, Taiwan

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2000年 / 2卷 / 04期

关键词：

D O I：

10.1021/cc0000085

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An expedient liquid-phase synthesis for construction of the diverse benzimidazole libraries is described. Nucleophilic aryl substitution of poly(ethylene glycol)-supported 4-fluoro-3-nitrobenzoic acid 3 with several primary amines under basic conditions, followed by Zn/NH4Cl mediated nitro group reduction, gave the PEG bound diamines 5. Subsequent cyclization of immobilized o-phenylenediamine 5 using thiocarbonyldiimidazole (TCD) or thiophosgene in dichloromethane furnished benzimidazole-2-thiones 6. Treatment of 6 with alkyl halides and benzylic halides in the presence of triethylamine provided 1-substituted-2-auyIthio5-carbamoylbenzimidazoles on the support. The desired products 8 were severed from the PEG under mild conditions in high yield and high purity.

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页码：341 / 348

页数：8

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