Phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles: access to 1,3-diazepine and 1,4-diazocine derivatives

Abstract

Novel methods for constructing functionalized 1,3-diazepine and 1,4-diazocine derivatives have been disclosed through phosphine-catalyzed [4 + 3] and [4 + 4] annulations of β′-acetoxy allenoates with N,N-dinucleophiles. These approaches demonstrate high efficiency and yields ranging from good to excellent. The biological evaluation indicates that three of the developed cycloadducts exhibit satisfactory inhibitory activities against three human cancer cell lines (HCT116, A549 and HepG2) beyond those of 5-fluorouracil.