β-Nitrostyrenes as a valuable precursor for the synthesis of β-aryl-γ-lactam and 2-oxo-1,2-dihydroquinoline derivatives

We successfully demonstrated two different reaction pathways for the synthesis of beta-aryl-gamma-lactam and 2-oxo-1,2-dihydroquinoline derivatives using beta-nitrostyrenes. The reaction strategy involves the Michael addition followed by reduction and cyclization reactions. Michael adducts containing two different nitro group such as one on aryl ring and another on side chain, selectively takes the path to involve nitro group on aryl to form 2-oxo-1,2-dihydroquinoline derivatives as cyclized product. Michael adducts with nitro group on side chain alone forms beta-aryl-gamma-lactam derivatives as cyclized product. This methodology is appealing with reliability and scalability with gram scale products that can be synthesized. These heterocyclic compounds can be exploited for their biological activity.

Automated summary

We have demonstrated two different reaction pathways for the synthesis of beta-aryl-gamma-lactam and 2-oxo-1,2-dihydroquinoline derivatives using beta-nitrostyrenes. This method is reliable and scalable for gram scale production, and the resulting compounds can be further explored for their biological activity.