A new piperidine‐catalyzed Groebke–Bienaymé–Blackburn (GBB) multicomponent reaction of 2‐aminobenzimidazoles, methyl 2‐formylbenzoate, and isocyanides has been explored. A facile and straightforward postmodification leads to isoquinolinone‐embedded imidazo[1,2‐a]benzimidazoles. Insight into a plausible mechanism is discussed and supported by X‐ray crystal structure analysis.
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.
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