Litcius/Paper detail

<scp>β‐Nitrostyrenes</scp> as a valuable precursor for the synthesis of β‐aryl‐γ‐lactam and 2‐oxo‐1,2‐dihydroquinoline derivatives

Dandamudi V. Lenin, D. C. PATEL, Payal Malvi

2022Journal of Heterocyclic Chemistry11 citationsDOI

Abstract

Abstract We successfully demonstrated two different reaction pathways for the synthesis of β‐aryl‐γ‐lactam and 2‐oxo‐1,2‐dihydroquinoline derivatives using β‐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 β‐aryl‐γ‐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.

Topics & Concepts

ChemistryArylNitroLactamAdductMichael reactionRing (chemistry)Side chainCombinatorial chemistryStereochemistryOrganic chemistryCatalysisPolymerAlkylSynthesis and Catalytic ReactionsSynthesis of β-Lactam CompoundsSynthetic Organic Chemistry Methods