Synthesis and structure of novel dithioderivatives of 3-pyrrolin-2-one

Unsaturated γ-lactams (3-pyrrolin-2-ones) are an important class of five-membered nitrogen-containing heterocycles that play a significant role as structural motifs in numerous natural products and synthesized compounds with a wide range of biological activities. These motifs are also successfully used as intermediates in organic transformations and allow access to more diverse compounds and previously inaccessible structures. In this work, method for the synthesis of two types of novel heterocyclic compounds containing an unsaturated γ-lactam ring and two sulfur atoms was developed. Reactive and easily available substrates of 5-methoxy-2(5H)-furanone series were involved into the reactions with ammonia and benzylamine and converted into the corresponding dithioderivatives of 5-hydroxy-3-pyrrolin-2-one, difficult to access by other methods. The molecular and crystal structures of four novel sulfur-containing compounds were characterized by single-crystal X-ray diffraction. These heterocyclic systems are promising candidates for further functionalization and biological screening.