Mild and Expeditious Synthesis of Sulfenyl Enaminones of l-α-Amino Esters and Aryl/Alkyl Amines through NCS-Mediated Sulfenylation.

ABSTRACT: Sulfenylation or selenylation of enaminones of l-α-amino esters requires mild reaction conditions due to the presence of a racemization-prone chiral center and reactive side chains. An N-chlorosuccinimide (NCS)-mediated methodology has been developed for rapid sulfenylation of enaminones of l-α-amino esters and aryl/alkyl amines at room temperature in open air under metal-free conditions. Enaminones of l-α-amino esters bearing aliphatic, aromatic, and heterocyclic side chains react efficiently with diverse aryl/alkyl/heteroaryl thiols (R¹SH) in the presence of NCS to afford a library of biologically important sulfenyl enaminones in good-to-excellent yields (71-90%). Under similar reaction conditions, the enaminones also react with benzeneselenol to produce selenyl enaminones in good yield (73-83%). The NCS-mediated pathway generates sulfenyl chloride (R¹SCl) as an intermediate which leads to rapid sulfenylation of enaminones through cross-dehydrogenative coupling (CDC) under mild reaction conditions.

SUBMITTER: Mukherjee S 

PROVIDER: S-EPMC8675011 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature