• Synthesis of 7-arylethyl-5-arylpyrazolo[1,5-a]pyrimidines through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer cascade

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    • Keywords


      Pyrazole-3-amine; dienone; pyrazolo[1, 5-a]pyrimidine; tandem reaction; heterocyclization.

    • Abstract


      An efficient method for the synthesis of pyrazolo[1,5-a]pyrimidines by the tandem reactions of dienones with pyrazole-3-amine through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer process in the presence of potassium hydroxide is described. This protocol offers access to 7-arylethyl-5-arylpyrazolo[1,5-a]pyrimidines in good to excellent yield. Meanwhile for 4-substituted dienones, different products, 7-arylethylene-5-arylpyrazolo[1,5-a]pyrimidines, are given through an aza-Michael addition/nucleophilic addition/oxidation process. A gram-scale reaction has been performed to demonstrate the potency of optimized procedure for the scale-up process.

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