Aza−Oxy−Carbanion Relay via Non-Brook Rearrangement: Efficient Synthesis of Furo[3,2-c]pyridinones

An aza−oxy−carbanion relay via tandem Michael addition/ring opening of cyclopropane and recyclization/carbanion migration/electrophile trapping has been developed by the utilization of 1-cinnamoylcyclopropanecarboxamides to react with various electrophiles. This represents the first example of anion relay chemistry via non-Brook rearrangement. This novel protocol has been applied in the facile and efficient synthesis of biologically active bicyclic furo[3,2-c]pyridinone compounds.