Synthesis of functionalized bicyclic pyridones containing dithiocarbamate group using thioazlactones, diamines and nitroketene dithioacetal

An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio) thioazlactones, diamines and nitro ketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation/intramolecular 1,4-addition-type Friedel-Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereselectively. The desired products are fully characterized by FT-IR, 1H and 13CNMR, CHN and single crystal X-ray diffraction analyses.