Arylation of enelactams using TIPSOTf: reaction scope and mechanistic insight was written by Idzik, Tomasz J.;Myk, Zofia M.;Struk, Lukasz;Peruzynska, Magdalena;Maciejewska, Gabriela;Drozdzik, Marek;Sosnicki, Jacek G.. And the article was included in Organic Chemistry Frontiers in 2021.Computed Properties of C11H9NO This article mentions the following:
A novel method for inter- and intramol. arylation of enelactams (3,4-dihydropyridin-2-ones), up to 99% yield, triggered by triisopropylsilyltrifluoromethanesulfonate (TIPSOTf) was proposed. It offered high synthetic usefulness, especially for synthesis of polycyclic systems, e.g., I obtained from conformationally rigid δ-enelactams, for which use of conventional method, involving cyclization by treatment with TfOH, failed. Multinuclear (1H, 13C, 19F and 29Si) NMR spectroscopy applied for reaction monitoring as well as DOSY NMR experiment permitted identification of intermediates and proposition of reaction mechanism. In process of checking scope of 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 ± 0.4μM) was evidenced. In the experiment, the researchers used many compounds, for example, 5-Phenylpyridin-2-ol (cas: 76053-45-7Computed Properties of C11H9NO).
5-Phenylpyridin-2-ol (cas: 76053-45-7) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Computed Properties of C11H9NO