Acetylene-free synthesis of vinyloxy pyridine and quinoline

作者：Hamdi Abdelrahman; Mostafa Amany S; Watat Cedric Nana; Laurent Mathieu Y; Ben Ayed Kawther; Selim Khalid B; Dujardin Gilles

来源：Tetrahedron Letters, 2016, 57(51): 5825-5829.

DOI：10.1016/j.tetlet.2016.11.061

• N-Heteroaryl vinyl ethers
• Copper-cross coupling
• Pyridines
• Quinolines
• Isoquinolines

Copper-catalyzed vinylation of 2- and 4-hydroxy pyridine and quinoline affords exclusively N-vinylation products. However, vinyl ethers of 4-hydroxy pyridine and quinoline can be prepared via a three-step sequence involving copper-catalyzed C-O cross coupling reaction of the corresponding N-heteroaryl bromides with ethylene glycol, chlorination of the terminal alcohol, and dehydrohalogenation of the beta-chloro ethers. Although not efficient in 2-hydroxy series, this method can be conveniently applied to the preparation of various aza-aryl vinyl ethers in moderate to good overall yields.

• 出版日期2016-12-21