101583-63-5

Upstream product

• 4945-26-0 2-styrylquinoline 
• 1613-41-8 2-phenethyl-quinoline 
• 100-42-5 styrene 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-63-4 2-methylquinoline 
• 53931-59-2 5-phenyl-1-penten-3-one 
• 38101-69-8 2-[(E)-styryl]quinoline 
• 2785-29-7 benzyl potassium 

Relevant academic research and scientific papers

Heterogeneous gold-catalyzed selective reductive transformation of quinolines with formic acid

Single phase rutile titania supported gold nanoparticles (Au/TiO2-R) are found to be efficient and versatile catalysts for chemo- and regioselective transfer hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines (THQs) using formic acid (FA) as a safe and convenient hydrogen source under mild conditions. The activity and chemoselectivity of the Au/TiO2-R catalyst towards THQs is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Furthermore, a straightforward and selective route to N-formyltetrahydroquinolines (FTHQ) directly from quinoline compounds and FA by one-pot, gold-catalyzed reductive N-formylation protocol is also established.

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

An efficient catalytic system for the hydrogenation of quinolines

A new catalytic system ([Ru(p-cymene)Cl2]2/I2) has been developed for the hydrogenation of quinoline derivatives with high reactivity. For the 2-methyl-quinoline, the hydrogenation reaction can proceed smoothly at an S/C of 20,000/1 with complete conversion. The iodine additive is important for the reactivity.

Unsupported nanoporous gold catalyst for highly selective hydrogenation of quinolines

For the first time, the highly efficient and regioselective hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines using unsupported nanoporous gold (AuNPore) as a catalyst and organosilane with water as a hydrogen source is reported. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity.

Boric acid catalyzed chemoselective reduction of quinolines

Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety. The reaction parameters and tentative mechanistic pathways are demonstrated by various control experiments and NMR studies. The present work can also be scaled up to obtain gram quantities and the utility of the developed process is illustrated by the transformation of 1,2,3,4-THQs into a series of biologically important molecules including the antiarrhythmic drug nicainoprol.

Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen

Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.

Silver-Catalyzed Reduction of Quinolines in Water

A ligand- and base-free silver-catalyzed reduction of quinolines and electron-deficient aromatic N-heteroarenes in water has been described. Mechanistic studies revealed that the effective reducing species was Ag-H. This versatile catalytic protocol provided facile, environmentally friendly, and practical access to a variety of 1,2,3,4-tetrahydroquinoline derivatives at room temperature.

Method for conducting catalytic hydrogenation on nitrogen-containing unsaturated heterocyclic compound

The invention provides a method for conducting catalytic hydrogenation on a nitrogen-containing unsaturated heterocyclic compound, and belongs to the technical field of catalytic hydrogenation. The provided method for conducting catalytic hydrogenation on the nitrogen-containing unsaturated heterocyclic compound comprises the following step: in the presence of hydrogen and a manganese catalyst, with the nitrogen-containing unsaturated heterocyclic compound as a substrate, carrying out a hydrogenation reaction. According to the method for conducting catalytic hydrogenation on the nitrogen-containing unsaturated heterocyclic compound, he adopted manganese catalyst is an NNP-type pincer manganese catalyst, has the advantages of being cheap, easy to obtain and low in toxicity compared with noble metal catalysts, has the advantages of being wide in substrate applicability and high in target product yield compared with an existing cheap metal iron catalyst or cobalt catalyst, and is higher in electron donating ability and smaller in steric hindrance compared with a PNP-type pincer manganese catalyst, and thus shows higher reaction activity in a series of hydrogenation reactions, and thetarget product yield is up to 99%.

A 2,6-bis(phenylamino)pyridinato titanium catalyst for the highly regioselective hydroaminoalkylation of styrenes and 1,3-butadienes

The C-C bond forming catalytic hydroaminoalkylation of terminal alkenes, 1,3-dienes, or styrenes allows a direct and highly atom efficient (100 %) synthesis of amines which can result in the formation of two regioisomers, the linear and the branched product. We present a new titanium catalyst with 2,6-bis(phenylamino)pyridinato ligands for intermolecular hydroaminoalkylation reactions of styrenes and 1-phenyl-1,3-butadienes that delivers the corresponding linear hydroaminoalkylation products with excellent regioselectivities. Linear progress: A new Ti complex with 2,6-bis(phenylamino) pyridinato ligands catalyzes highly regioselective hydroaminoalkylation reactions of styrenes. The process that directly gives access to the corresponding linear hydroaminoalkylation products offers a new and flexible synthetic approach towards pharmaceutically important 3-arylpropylamines. It is also possible to convert (E)-1-phenyl-1,3-butadienes into the corresponding linear products.

Catalytic hydrogenation with frustrated lewis pairs: Selectivity achieved by size-exclusion design of lewis acids

Catalytic hydrogenation that utilizes frustrated Lewis pair (FLP) catalysts is a subject of growing interest because such catalysts offer a unique opportunity for the development of transition-metal-free hydrogenations. The aim of our recent efforts is to further increase the functional-group tolerance and chemoselectivity of FLP catalysts by means of size-exclusion catalyst design. Given that hydrogen molecule is the smallest molecule, our modified Lewis acids feature a highly shielded boron center that still allows the cleavage of the hydrogen but avoids undesirable FLP reactivity by simple physical constraint. As a result, greater latitude in substrate scope can be achieved, as exemplified by the chemoselective reduction of α,β-unsaturated imines, ketones, and quinolines. In addition to synthetic aspects, detailed NMR spectroscopic, DFT, and 2H isotopic labeling studies were performed to gain further mechanistic insight into FLP hydrogenation. Copyright