40624-66-6

Upstream product

• 91-22-5 quinoline 
• 591-51-5 phenyllithium 
• 100-58-3 phenylmagnesium bromide 
• 612-18-0 1,2-dihydroquinoline 
• 612-96-4 2-Phenylquinoline 

Downstream Products

• 98847-83-7 (4-Nitro-phenyl)-(2-phenyl-2H-quinolin-1-yl)-methanone 
• 98847-84-8 (3,5-Dinitro-phenyl)-(2-phenyl-2H-quinolin-1-yl)-methanone 
• 612-96-4 2-Phenylquinoline 
• 758640-21-0 N-Benzylaniline 
• 1393654-13-1 4-phenyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione 
• 98847-85-9 (4-Methoxy-phenyl)-(2-phenyl-2H-quinolin-1-yl)-methanone 
• 36072-73-8 1-(benzoyl)-2-phenyl-1,2-dihydroquinoline 
• 24005-23-0 2-phenyl-1,2,3,4-tetrahydroquinoline 
• 37777-35-8 N-Acetyl-2-phenyl-1,2-dihydrochinolin 
• 98847-86-0 2-phenylquinolinium perchlorate 

Relevant academic research and scientific papers

Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines

A Ni-catalyzed asymmetric hydrocyanation that enables the formation of 4-cyanotetrahydroquinolines in good yields with excellent enantioselectivities is presented herein. A variety of functional groups are well-tolerated, and a gram-scale reaction supports the synthetic potential of the transformation. Additionally, several crucial intermediates for pharmaceutically active agents, including a PGD2 receptor antagonist, are now accessible through asymmetric synthesis using this new protocol.

Iron-Catalyzed Aerobic Dehydrogenative Kinetic Resolution of Cyclic Secondary Amines

A nonenzymatic iron-catalyzed dehydrogenative kinetic resolution of cyclic secondary amines using air as an oxidant has been reported. The economical and practical method is applicable to a series of cyclic benzylic amines, including 5,6-dihydrophenanthridines and 1,2-dihydroquinolines, with diverse functional groups at the α position in high yields with excellent enantioselectivities. The direct dehydrogenative kinetic resolution of advanced intermediates of bioactive molecules that are difficult to access using existing catalytic asymmetric synthetic strategy was also demonstrated.

Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular hydrogen proceeded in high to excellent yields for N-protected indolines as well as four other substrate classes. The mechanism of this unprecedented FLP-catalyzed reaction was investigated by mechanistic studies, characterization of reaction intermediates by NMR spectroscopy and X-ray crystal analysis, and by quantum-mechanical calculations. Hydrogen liberation from the ammonium hydridoborate intermediate is the rate-determining step of the oxidation. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28 through a second catalytic cycle.

Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2- diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

To further expand the structure-cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 μM) after 24 h.

Highly active metal-free catalysts for hydrogenation of unsaturated nitrogen-containing compounds

New highly active ansa-ammonium borate catalysts for the direct metal-free hydrogenation of imines were prepared by tuning of the basicity and steric bulkiness of their amine moieties. The highest catalytic activity among previously reported organocatalytic systems was shown for a wide range of nitrogen-containing substrates. The first example of asymmetric imine hydrogenation based on the ansa-ammonium borate concept was demonstrated. Furthermore, effective catalyst recovery by extraction of the acidic solution with an organic solvent followed by dehydration with TMSBr was elaborated. The initial findings highlight the development of more effective chiral ansa-ammonium borates for enantioselective hydrogenation. Therefore, the progress achieved in the ansa-ammonium borate concept makes it very promising for further elaboration with the aim to obtain industrially applicable catalysts. Copyright

Synthesis, Structure-Activity Relationships, and Pharmacological Evalaution of Pyrroloquinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhitory Properties. Potential Therapeutic Application in Asthma

A series of pyrroloquinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma.The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-ethyl chain in conjuction with a methyl group on the 2-position for potent antagonism of both histamine and PAF.The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF.This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-ethyl>-4H-pyrroloquinoline (24, KC 11404) which was found to be active against all three of the selected mediators.Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED50=1.9 and 2.1 μmol/kg, respectively).When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.

7-fused 2-(piperazinoalkyl) indole derivatives, intermediates and compositions thereof

Pharmacologically active compounds having anti-allergic properties corresponding to the formula I STR1 which can be mono- or disubstituted in the phenyl ring and their acid addition salts and/or S-mono- or dioxides of sulfur-containing compounds of the formula I are described, together with processes and intermediates for their preparation.

On the mechanism of disproportionation reactions of 1,2-dihydroquinolines

The commonly accepted mechanism for the acid-catalyzed disproportionation of 1,2-dihydroquinolines involves a hydride transfer from C-2 of one dihydroquinoline molecule to C-4 of another molecule which has already been protonated at C-3.This mechanism is shown to be incorrect.The proposed intermediate is shown to react by solvent addition and not by reduction under the conditions of the reaction.Evidence has been obtained which shows that the reaction proceeds by way of a 3,4-dihydroquinoline intermediate.A possible mechanism for the formation of the intermediate is discussed.