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Note | Special issue | Vol 66, No. 1, 2005, pp.611-619
Published online, 21st October, 2005
DOI: 10.3987/COM-05-S(K)48
One-Step Synthesis of Ethyl Quinaldates by Lewis Acid Catalyzed Three-Component Coupling Reaction of Aromatic Amines, Aliphatic Aldehydes and Ethyl Glyoxylate

Takashi Inada, Takayuki Nakajima, and Isao Shimizu*

*School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


A convenient, efficient and simple one-pot method for the synthesis of quinaldates was developed by three-component coupling reaction of an arylamine (1), ethyl glyoxylate and an aliphatic aldehyde (2) in the presence of Lewis acid catalyst. The reaction proceeded most effectively using Yb(OTf)3 as a catalyst.