5263-87-6Relevant articles and documents
A NOVEL ROUTE TO QUINOLINE DERIVATIVES FROM 1,3-PROPANEDIOL AND AMINOARENES: RUTHENIUM CATALYZED HETEROCYCLIZATION UNDER NON-ACIDIC CONDITIONS
Tsuji, Yashushi,Nishimura, Hideo,Huh, Keun-Tae,Watanabe, Yoshihisa
, p. C44 - C46 (1985)
Ruthenium trichloride hydrate combined with tributylphosphine catalyzes the reaction between 1,3-propanediol and an aminoarene at 180 deg C, providing a novel route to quinoline derivatives under non-acidic conditions.
Organocatalytic Enantioselective Functionalization of Hydroxyquinolines through an Aza-Friedel-Crafts Alkylation with Isatin-derived Ketimines
Vila, Carlos,Rendón-Pati?o, Alejandra,Montesinos-Magraner, Marc,Blay, Gonzalo,Mu?oz, M. Carmen,Pedro, José R.
, p. 859 - 864 (2018)
A highly enantioselective addition of hydroxyquinolines to isatin-derived ketimines has been realized using a quinine-derived thiourea organocatalyst. The reaction affords chiral 3-amino-2-oxindoles bearing a quinoline moiety with a quaternary stereocenter in high yields (up to 98%) and excellent enantioselectivities (up to 99%). Moreover, we can extend this methodology for the enantioselective functionalization of 5-hydroxyisoquinoline. This methodology represents, to the best of our knowledge, the first enantioselective addition of hydroxyquinolines to imines. (Figure presented.).
Picomole-Scale Real-Time Photoreaction Screening: Discovery of the Visible-Light-Promoted Dehydrogenation of Tetrahydroquinolines under Ambient Conditions
Chen, Suming,Wan, Qiongqiong,Badu-Tawiah, Abraham K.
, p. 9345 - 9349 (2016)
The identification of new photocatalytic pathways expands our knowledge of chemical reactivity and enables new environmentally friendly synthetic applications. However, the development of miniaturized screening procedures/platforms to expedite the discovery of photochemical reactions remains challenging. Herein, we describe a picomole-scale, real-time photoreaction screening platform in which a handheld laser source is coupled with nano-electrospray ionization mass spectrometry. By using this method, we discovered an accelerated dehydrogenation pathway for the conversion of tetrahydroquinolines into the corresponding quinolines. This transformation is readily promoted by an off-the-shelf [Ru(bpy)3]Cl2?6 H2O complex in air at ambient temperature in direct sunlight, or with the aid of an energy-saving lamp. Moreover, radical cations and trans-dihydride intermediates captured by the screening platform provided direct evidence for the mechanism of the photoredox reaction.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
supporting information, p. 2876 - 2894 (2021/02/01)
Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
