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Published on: June 10, 2021
Visible-Light-Driven Synthesis of Pyrrolo[3,4-b]quinolin-1-one Imines Exhibiting Aggregation-Induced Enhanced
Chinnagounder Kameshwaran1, Fazlur-Rahman Nawaz Khan1
1Organic and Medicinal Research Laboratory, School of Advanced Sciences, Department of Chemistry, Vellore Institute of Technology, Vellore, 632014, India.
Abstract:
In recent years, visible light-mediated transformations have gained significant attention. In this work, we report the synthesis of N-substituted 2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones via a one-pot strategy involving C(sp3)-H functionalization, cyclization, and condensation to form the corresponding imines under visible-light conditions. Furthermore, the imines exhibited Aggregation-Induced Enhanced Emission (AIEE) properties and favorable photophysical response toward metal ions. Subsequent metal-free aerobic oxidation of these imines in the presence of a peroxide medium afforded the corresponding amides. The synthetic utility of this protocol was further demonstrated through post-functionalization of the products and gram-scale synthesis.
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