119225-99-9Relevant academic research and scientific papers
An intramolecular C-N cross-coupling of β-enaminones: A simple and efficient way to precursors of some alkaloids of Galipea officinalis
Douov, Hana,Hork, Radim,Ruikov, Zdeka,imunek, Petr
, p. 884 - 892 (2015/08/24)
2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.
Asymmetric tandem reduction of 2-(aroylmethyl)quinolines with phosphine-free Ru-TsDPEN catalyst
Wang, Tianli,Ouyang, Guanghui,He, Yan-Mei,Fan, Qing-Hua
scheme or table, p. 939 - 942 (2011/06/17)
The phosphine-free ruthenium complex containing chi-ral N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (TsDPEN) showed excellent stereoselectivity in the tandem asymmetric reduction of 2-(aroylmethyl) quinolines. The reaction involves transfer hydrogenation of aromatic ketones and hydrogenation of quinolines, giving 1,2,3,4-tetrahydroquinoline derivatives with up to 99% ee and 95:5 dr. Georg Thieme Verlag Stuttgart · New York.
Highly enantioselective iridium-Catalyzed hydrogenation of 2-Benzylquinolines and 2-Functionalized and 2,3-disubstituted quinolines
Wang, Da-Wei,Wang, Xiao-Bing,Wang, Duo-Sheng,Lu, Sheng-Mei,Zhou, Yong-Gui,Li, Yu-Xue
supporting information; experimental part, p. 2780 - 2787 (2009/08/08)
The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinohnes was developed by using the [Ir(COD)Cl]2/bisphosphine/I2 system with up to 96% ee. Moreover, mechanistic studies revealed the hydrogenation mechanism of quinoline involves a 1,4-hydride addition, isomerization, and 1,2-hydride addition, and the catalytic active species may be a Ir(III) complex with chloride and iodide.
TAUTOMERISM IN 2-KETOMETHYL QUINOLINES
Greenhill, John V.,Loghmani-Khouzani, Hossein,Maitland, Derek J.
, p. 3319 - 3326 (2007/10/02)
The i.r. solution spectra of a series of 2-ketomethylquinolines have been studied.Tautomeric ratios have been determined by n.m.r. spectroscopy.With one exception the compounds were substantially or exclusively in the enaminone forms.The only compound carrying an α-methyl group (18) proved to be solely in the ketone form.
