Transition-Metal-Free Alkylation and Acylation of Benzoxazinones with 1,4-Dihydropyridines

The direct functionalization of N-heterocycles is a vital transformation for the development of pharmaceuticals, functional materials, and other chemical entities. Herein, the transition-metal-free alkylation and acylation of C(sp(2))-H bonds in biologically relevant 2-benzoxazinones with 1,4-dihydropyridines as readily accessible radical surrogates is described. Excellent functional group compatibility and a broad substrate scope were attained. Gram- scale reaction and transformations of the synthesized adducts via Suzuki coupling with heteroaryl boronic acids demonstrated the synthetic potential of the developed protocol.

Automated summary

The study focuses on the transition-metal-free alkylation and acylation of C(sp(2))-H bonds in biologically relevant 2-benzoxazinones using 1,4-dihydropyridines as radical surrogates. The research demonstrates excellent functional group compatibility and a broad substrate scope. Additionally, gram-scale reaction and transformations of the synthesized adducts via Suzuki coupling with heteroaryl boronic acids highlights the synthetic potential of the developed protocol.