A concise synthesis of 2-(2-aminothiophene)-benzimidazoles by one-pot multicomponent reaction

Li Hsun Chen, Ying Sheng Chuang, Bharat D. Narhe, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A one-pot synthesis of 2-aminothiophene linked benzimidazoles was achieved by utilizing 2-cyanomethyl benzimidazoles in a modified Gewald multicomponent reaction. The synthetic strategy of the reaction involved treatment of 2-(cyanomethyl)-benzimdazole with aldehydes containing an active methylene group and sulfur powder under refluxing conditions. The multicomponent reaction proceeded via Knoevenagel condensation of 2-(cyanomethyl)-benzimdazole with aldehyde to generate an α,β-unsaturated nitrile followed by cyclization with molecular sulfur under basic conditions to give biologically relevant 2-(2-aminothiophene)-benzimidazoles in good yields.

Original languageEnglish
Pages (from-to)13934-13943
Number of pages10
JournalRSC Advances
Volume3
Issue number33
DOIs
StatePublished - 7 Sep 2013

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