Yb(OTf)₃-catalyzed cyclization of an N-silylenamine with 2-methylene-1,3-cyclohexanedione to afford a 7,8-dihydroquinolin-5(6H)-one derivative and its application to the one-pot conversion to a 2,3,5-trisubstituted quinoline derivative

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• 作者：Norio Sakai ; Daisuke Aoki ; Toshihiro Hamajima and Takeo Konakahara
• 关键词：N-Silylenamine ; 7 ; 8-Dihydroquinolin-5-one ; Quinoline ; Ytterbium triflate
• 刊名：Tetrahedron Letters
• 出版年：2006
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：20 February 2006
• 卷：47
• 期：8
• 页码：1261-1265
• 文件大小：122 K

摘要

A catalytic amount of ytterbium triflate (Yb(OTf)₃) promotes the cyclization of an N-silylenamine with in situ generated 2-methylene-1,3-cyclohexanedione and 2-methylenecyclohexanone to produce the corresponding 2,3-disubstituted 7,8-dihydroquinolin-5-one and 5,6,7,8-tetrahydroquinolin-5-one in moderate to good yields. A one-pot conversion of 7,8-dihydroquinolin-5-one to the quinoline derivative also proceeded in good yield.