Summary
1.
By the free-radical addition of thiols to N-vinyl and N-allyl lactams in presence of azodiisobutyronitrile 1-[2-(alkylthio)ethyl]-2-pyrrolidinones, N-2-(alkylthio)ethylcaprolactams, 1-[3-(alkylthio)propyl]-2-pyrrolidinones, and N-3-(alkylthio)propylcaprolactams were synthesized in 70–95% yield. In this reaction N-vinyl lactams are more reactive than N-allyl lactams; moreover, in each of these groups of N-alkenyl lactams, caprolactam derivatives are a little more active.
2.
By the reaction of 1-(2-chloroproyl)-2-pyrrolidinone with sodium alkyl sulfides, pyrrolidinone and 1-[2-[(ethoxycarbonyl)methylthio]propyl]-2-pyrrolidinone were synthesized.
3.
N-2-[(ethoxycarbonyl)methylthio]ethyl and N-3-[(ethoxycarbonyl)methylthio]propyl lactams are precursors in the biosynthesis of new penicillins.