Synthesis of Highly Substituted 3-Pyrrolin-2-ones from N,N-Disubstituted α-Amino Acids

Highly functionalized 5-membered N-heterocyclic compounds, 4-aryl-3-chloro-5-methoxy-1-methyl-3-pyrrolin-2-ones, have been synthesized in moderate to high yields by the reaction of N,N-dimethylated aromatic alpha-amino acids with oxalyl chloride, followed by solvolysis with MeOH. The products possess a number of functional groups such as an amide, a mixed amido/alkoxy acetal, a vinyl halide, and an alkene and thus are promising candidates to be used as starting materials for the synthesis of diverse five-membered N-heterocyclic compounds.