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One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent
Sundararajan Suresh1, Fazlur Rahman Nawaz Khan1
1Organic and Medicinal Chemistry Research Laboratory, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, Tamil Nadu, India.
Abstract:
The sequential synthesis of N-heterocycles from saturated ketones poses significant challenges and has rarely been reported. Herein, an efficient synthesis of alkenylated dihydroquinolinones 7 and hexahydroacridinones 8 is achieved from saturated ketones 1 or 2 via dehydrogenation, cyclization, oxidation, and α-alkenylation in choline chloride-based deep eutectic solvent (DES) medium. This strategy provides alkenylated dihydroquinolinones 7 and hexahydroacridinones 8 in excellent yield from low-cost, readily available starting materials under environmentally benign conditions. Furthermore, the synthesized compounds (4, 5, 7, and 8) were investigated for their photophysical properties through absorption and emission spectral studies.
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