Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence.

Wei-Shun Hsu, Min-Huan Tsai, Indrajeet J Barve, Gorakh S Yellol, Chung-Ming Sun

ACS combinatorial science 2017 Jul 10

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A condition-based skeletal divergent synthesis was explored to achieve skeletal diversity in two component condensation reaction. Cyanomethyl benzimidazole was reacted with α-bromoketone under thermal conditions to furnish 2-aminofuranyl-benzimidazoles, while the same reaction afforded 3-cyano-benzopyrrolo-imidazoles under microwave irradiation. Two nonequivalent nucleophilic centers on benzimidazole moiety were manipulated elegantly by different reaction conditions to achieve the skeletal diversity.

Citation

Wei-Shun Hsu, Min-Huan Tsai, Indrajeet J Barve, Gorakh S Yellol, Chung-Ming Sun. Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence. ACS combinatorial science. 2017 Jul 10;19(7):492-499