Visible-light-induced [1,3]-brook rearrangements of α-ketoacylsilanes and their subsequent trapping in a tandem annulation with 1,3,5-triazinanes and azomethine imines

Abstract

An unusual visible-light-induced [1,3]-Brook rearrangement of α-ketoacylsilanes for cascade cyclization with 1,3,5-triazinanes and C,N-cyclic azomethine imines has been developed under catalyst-free and mild reaction conditions. The strategy offers an efficient and convenient approach for the rapid assembly of various β-lactams and pyrazolidinone scaffolds with structural and functional importance. Moreover, continuous-flow chemistry has been employed for two photochemical processes and gram-scale syntheses (up to 100 times) with comparable efficiency to batch conditions in a relatively short time, which allowed high-throughout synthesis and exhibited an increase in productivity.