Copper-Catalyzed Oxidative [1+2+1+2] Cascade Cyclization of N,N-Dimethyl Enaminones with Benzylamines: A Facile Access to Functionalized 1,4-Dihydropyridines

Using benzylamines as the C4 source of 1,4-dihydropyridines (1,4-DHPs), a Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for the synthesis of 1,4-DHPs was firstly developed. A broad range of easily available N,N-dimethyl enaminones and benzylamines are employed smoothly to provide a diverse range of 1,4-DHPs with high efficiency. This method is performed by a one-pot cascade C(sp(3))-H bond functionalization/C(sp(3))-N cleavage/cyclization strategy to form simultaneously two C(sp(3))-C(sp(2)) bonds, two C(sp(2))-N bonds, and a 1,4-DHP ring.

Automated summary

A Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for the synthesis of 1,4-DHPs was developed using benzylamines as the C4 source. A wide range of N,N-dimethyl enaminones and benzylamines were smoothly employed to provide diverse 1,4-DHPs with high efficiency. This method utilizes a one-pot cascade C(sp(3))-H bond functionalization/C(sp(3))-N cleavage/cyclization strategy to simultaneously form two C(sp(3))-C(sp(2)) bonds, two C(sp(2))-N bonds, and a 1,4-DHP ring.