Efficient Friedländer Synthesis of Quinoline Derivatives from 2-Aminoarylketones and Carbonyl Compounds Mediated by Recyclable PEG-Supported Sulfonic Acid

Abstract

2-Aminoarylketones undergo smooth condensation with α-methylene ketones in the presence of 10 mol% of poly(ethylene glycol) (PEG)–supported sulfonic acid under mild reaction conditions to afford the corresponding poly-substituted quinolines in excellent yields. The catalyst can be recovered by simple filtration and can be recycled in subsequent reactions. The method is simple, cost-effective, and environmentally benign.

Keywords:

• 2-Aminoarylketone
• α-methyleneketone
• PEG-supported sulfonic acid
• quinoline

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation (NSF) of China (No. 20562005), NSF of Jiangxi Province (Nos. 0620021 and 2007GZW0185), and the Research Program of Jiangxi Province Department of Education (No. GJJ08165).

Notes

^a Yields refer to pure isolated products.

^b Concd. H₂SO₄ used instead of PEG-bound sulfonic acid.

^a Yields refer to pure isolated products.