Tetrahedron Letters

Efficient synthesis of substituted quinolines through intramolecular addition of aryl anion to carbonyl carbon

Y Kobayashi, J Igarashi, C Feng

文献索引：Kobayashi, Yuichi; Igarashi, Junji; Feng, Chao; Toshifumi; Tojo Tetrahedron Letters, 2012 , vol. 53, # 29 p. 3742 - 3745

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被引用次数: 6

摘要

Substituted quinolines were synthesized in three steps from the Boc amides of substituted 2- iodoanilines and alkyl vinyl ketones. This method consists of (1) N-Michael addition of the Boc amide of 2-iodoaniline to alkyl vinyl ketone in the presence of Cs2CO3 in MeCN;(2) I– Mg exchange of the adduct with 3.5 equiv of i-PrMgCl· LiCl, and (3) acid-catalyzed reaction (excess AcCl in EtOH) of the resulting alcohol. Six examples are given with good yields.