A Novel and efficient base–promoted one–pot reaction of ynones with 2–aminobezonitriles is described. The reaction initiated through sequential aza–Michael addition/intramolecular cascade cyclization to afford various multisubstituted 4–aminoquinolines and 4–amino[1,8]naphthyridines in good to excellent yields. Operational simplicity, high atom–economy with broad substrate scope makes this protocol more attractive. In addition, the gram–scale synthesis and further transformation of the product were studied. 2–Haloarylyones as substrate provide N–arylquinolones as sole product.

Base-promoted synthesis of polysubstituted 4–aminoquinolines from ynones and 2–aminobenzonitriles under transition-metal-free conditions

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27th CRSI National Symposium in Chemistry

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