Functional rearrangement of 3-Cl or 3,3-diCl-γ-lactams bearing a secondary 1-chloroalkyl substituent at C-4

Abstract

The study of the reaction with MeONa/MeOH of chlorinated γ-lactams, prepared from the atom transfer radical cyclization of N-allyl-α-perchloroamides, has been extended to the case of substrates carrying an exo halogen atom on a branched carbon. Only with secondary exo C–Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, which with trichloro-lactams can proceed further to give 4-alkylidene derivatives. From a practical point of view, the outcome of the reaction with di- or trichloro N-cinnamylamides is synthetically valuable, affording the 5-methoxy-1H-pyrrol-2(5 H)-one or 3-benzylidenepyrrolidine-2,5-dione, respectively, in good to excellent yield.