Liquid-phase synthesis of 2-(alkylthio) benzimidazoles

Chih Ming Yeh; Chung-Ming Sun

doi:10.1016/S0040-4039(99)01487-2

Liquid-phase synthesis of 2-(alkylthio) benzimidazoles

Chih Ming Yeh, Chung-Ming Sun^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

An efficient liquid-phase synthesis of 2-alkylthio-5-carbamoylbenzimidazoles 1 is described. Immobilized o-fluoronitrobenzene 2 undergoes nucleophilic addition of primary amine to afford o-nitroaniline derivatives 3. Subsequent reduction of the aromatic nitro group followed by cyclization gives a PEG-bound benzimidazole-2-thione 5. S-Alkylation of polymer-supported scaffold 5 followed by cleavage gives the resulting library in high yield and high purity.

Original language	English
Pages (from-to)	7247-7250
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4039(99)01487-2
State	Published - 1 Oct 1999

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title = "Liquid-phase synthesis of 2-(alkylthio) benzimidazoles",

abstract = "An efficient liquid-phase synthesis of 2-alkylthio-5-carbamoylbenzimidazoles 1 is described. Immobilized o-fluoronitrobenzene 2 undergoes nucleophilic addition of primary amine to afford o-nitroaniline derivatives 3. Subsequent reduction of the aromatic nitro group followed by cyclization gives a PEG-bound benzimidazole-2-thione 5. S-Alkylation of polymer-supported scaffold 5 followed by cleavage gives the resulting library in high yield and high purity.",

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N2 - An efficient liquid-phase synthesis of 2-alkylthio-5-carbamoylbenzimidazoles 1 is described. Immobilized o-fluoronitrobenzene 2 undergoes nucleophilic addition of primary amine to afford o-nitroaniline derivatives 3. Subsequent reduction of the aromatic nitro group followed by cyclization gives a PEG-bound benzimidazole-2-thione 5. S-Alkylation of polymer-supported scaffold 5 followed by cleavage gives the resulting library in high yield and high purity.

AB - An efficient liquid-phase synthesis of 2-alkylthio-5-carbamoylbenzimidazoles 1 is described. Immobilized o-fluoronitrobenzene 2 undergoes nucleophilic addition of primary amine to afford o-nitroaniline derivatives 3. Subsequent reduction of the aromatic nitro group followed by cyclization gives a PEG-bound benzimidazole-2-thione 5. S-Alkylation of polymer-supported scaffold 5 followed by cleavage gives the resulting library in high yield and high purity.

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