Arylation of enelactams using TIPSOTf: reaction scope and mechanistic insight
文献信息
发布日期
2020-12-07
DOI
10.1039/D0QO01396J
影响因子
5.281
作者
Tomasz J. Idzik, Zofia M. Myk, Łukasz Struk, Magdalena Perużyńska, Gabriela Maciejewska, Marek Droździk, Jacek G. Sośnicki
查看原文
摘要
A novel method for the inter- and intramolecular arylation of enelactams (3,4-dihydropyridin-2-ones), up to 99% yield, triggered by triisopropylsilyltrifluoromethanesulfonate (TIPSOTf) is proposed. It offers high synthetic usefulness, especially for the synthesis of polycyclic systems obtained from conformationally rigid δ-enelactams, for which the use of the conventional method, involving cyclization by treatment with TfOH, failed. Multinuclear (1H, 13C, 19F and 29Si) NMR spectroscopy applied for the reaction monitoring as well as DOSY NMR experiment permitted identification of the intermediates and proposition of the reaction mechanism. In the process of checking the scope of the method application, condensed and bridged polycyclic piperidin-2-ones, including a derivative of alangiifoliumine A, were obtained. The inhibition of malignant melanoma A375 cell proliferation by some benzoquinolizidine derivatives (up to IC50 = 5.3 ± 0.4 μM) was evidenced.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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