Synthesis of new 3-(2,2,2-trifluoroethyl)-5-hydroxy-5-(phenylsulfanyl- or phenylsulfonyl-methyl)-1,5-dihydropyrrol-2-ones starting from α,β-unsaturated γ-lactones and primary amines

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• 作者：Jean-Philippe Bouillon ; Yuriy Shermolovich ; Sergiy Mykhaylychenko ; Dominique Harakat ; Bernard Tinant
• 关键词：Fluorine ; γ ; -Ketothioester ; Heterocycle ; γ ; -Lactam ; 1 ; 5-Dihydropyrrol-2-one
• 刊名：Journal of Fluorine Chemistry
• 出版年：2007
• 期刊代码：52_00221139
• 类别：ch
• 出版时间：August 2007
• 卷：128
• 期：8
• 页码：931-937
• 文件大小：410 K

摘要

The paper presents an efficient and straightforward transformation of α,β-unsaturated γ-lactones into 2,2,2-trifluoroethyl substituted γ-lactams, starting from a variety of primary amines. The structures of all new compounds were ascribed using 1D NMR (<sup>19sup>F, <sup>1sup>H, <sup>13sup>C), IR, MS. Selected <sup>19sup>F, <sup>13sup>C NMR and IR data of γ-lactams were compared to those of one which was characterized by X-ray diffraction analysis. The possible mechanism for the formation of γ-lactams is also presented.