Exploring the Synthetic Potential of γ-Lactam Derivatives Obtained from a Multicomponent Reaction-Applications as Antiproliferative Agents.

ABSTRACT: A study on the reactivity of 3-amino α,β-unsaturated γ-lactam derivatives obtained from a multicomponent reaction is presented. Key features of the substrates are the presence of an endocyclic α,β-unsaturated amide moiety and an enamine functionality. Following different synthetic protocols, the functionalization at three different positions of the lactam core is achieved. In the presence of a soft base, under thermodynamic conditions, the functionalization at C-4 takes place where the substrates behave as enamines, while the use of a strong base, under kinetic conditions, leads to the formation of C-5-functionalized γ-lactams, in the presence of ethyl glyoxalate, through a highly diastereoselective vinylogous aldol reaction. Moreover, the nucleophilic addition of organometallic species al

SUBMITTER: Lopez-Frances A 

PROVIDER: S-EPMC9182551 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature