Selective Synthesis of N-Substituted 1,2-Dihydropyridines from Furans by Copper-Induced Concurrent Tandem Catalysis

摘要

A novel transformation in which mono- or dialkyl-substituted furans are converted inton1,2-dihydropyridines upon reaction with PhIdNTs at room temperature is reported. The reaction is catalyzednby complexes of general formula TpxM (M ) Cu, Ag) and consists of a one-pot procedure with fournconsecutive catalytic cycles. Furan aziridination is followed by aziridine ring-opening, transimination reaction,ninverse-electronic-demand aza-Diels-Alder reaction, and a final hydrogen elimination reaction. Thenmechanism of the overall transformation is proposed where the metal complex displays a crucial role alongnthe reaction pathway.