Abstract
Liquid phasel synthesis of biheterocyclic benzimidazoles by controlled microwave irradiation was investigated. Polymer immobilized o-phenylenediamines was synthesized under microwave irradiation. The resulting PEG bound diamines was N-acylated with 4-fluoro-3-nitrobenzoic acid selectively in primary aromatic amino moiety. Nucleophilic aromatic substitution of amide was performed with various amines then cyclized to form the first benzimidazole scaffold in acidic condition. Successive reduction, cyclization with isothiocyanates yielded 5-(benzimidazol-2-yl)benzimidazoles. The desired products were released from the polymer support to afford the tri-substituted bis-benzimidazoles in good yields and purity.
Keywords: microwave irradiation, biheterocyclic benzimidazole, combinatorial synthesis
Combinatorial Chemistry & High Throughput Screening
Title: Combinatorial Synthesis of Biheterocyclic Benzimidazoles by Microwave Irradiation
Volume: 7 Issue: 3
Author(s): Wen-Bing Yeh, Mei-Jung Lin and Chung-Ming Sun
Affiliation:
Keywords: microwave irradiation, biheterocyclic benzimidazole, combinatorial synthesis
Abstract: Liquid phasel synthesis of biheterocyclic benzimidazoles by controlled microwave irradiation was investigated. Polymer immobilized o-phenylenediamines was synthesized under microwave irradiation. The resulting PEG bound diamines was N-acylated with 4-fluoro-3-nitrobenzoic acid selectively in primary aromatic amino moiety. Nucleophilic aromatic substitution of amide was performed with various amines then cyclized to form the first benzimidazole scaffold in acidic condition. Successive reduction, cyclization with isothiocyanates yielded 5-(benzimidazol-2-yl)benzimidazoles. The desired products were released from the polymer support to afford the tri-substituted bis-benzimidazoles in good yields and purity.
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Cite this article as:
Yeh Wen-Bing, Lin Mei-Jung and Sun Chung-Ming, Combinatorial Synthesis of Biheterocyclic Benzimidazoles by Microwave Irradiation, Combinatorial Chemistry & High Throughput Screening 2004; 7 (3) . https://dx.doi.org/10.2174/1386207043328878
DOI https://dx.doi.org/10.2174/1386207043328878 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
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