16600-51-4

Upstream product

• 529-23-7 o-aminobenzaldehyde 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 1115592-58-9 (1-chloro-3,4-dihydro-naphthalen-2-ylmethylene)-phenylamine 
• 1115592-61-4 1-(phenylamino)-3,4-dihydro-naphthalene-2-carbaldehyde 
• 1115592-64-7 1-phenylamino-2-(phenylimino)methyl-3,4-dihydro-naphthalene hydrochloride 
• 612-25-9 2-Nitrobenzyl alcohol 
• 28353-74-4 (E)-3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime 
• 446-52-6 2-Fluorobenzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 28353-74-4 3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime 
• 946844-57-1 2-(2-vinylphenyl)quinoline 

Downstream Products

• 225-51-4 benz[c]acridine 

Relevant academic research and scientific papers

Iridium-catalyzed synthesis of quinolines from 2-aminobenzyl alcohols with secondary alcohols

The quinoline derivatives were synthesized from 2-aminobenzyl alcohols and secondary alcohols by the direct one-step synthesis using the iridium complexes as catalyst. This efficient and easy method is suitable for all kinds of substituted quinolines.

An improved synthesis of quinolines from β-bromovinyl aldehydes and primary arylamines in the presence of a palladium catalyst

β-Bromovinyl aldehydes are effectively cyclized with primary arylamines in DMF at 110 °C in the presence of a catalytic amount of a palladium catalyst to give the corresponding quinolines in high yields. Copyright

Low-valent titanium reagent-promoted intramolecular reductive coupling reactions of ketomalononitriles: A facile synthesis of benzo[4,5]indene, acridine and quinoline derivatives

The intramolecular reductive coupling reactions of ketomalononitriles induced by a low-valent titanium reagent were studied. Benzo[4,5]indene, acridine and quinoline derivatives are prepared in good yields under neutral and mild conditions.

Efficient red phosphorescent Ir(iii) complexes based on rigid ligands with high external quantum efficiency and low efficiency roll-off

The rigid ligands in red phosphorescent Ir(iii) complexes can suppress the vibration and rotation around metal ions to maximize the utilization of low energy singlet and triplet states, thus greatly reducing the probability of non-radiative decay. In this paper, the coordination groups (phenyl and quinolinyl) are fused by a cyclohexyl group to produce rigidified ligands (5,6-dihydro-benzo[c]acridine and 9-fluoro-5,6-dihydro-benzo[c]acridine). A bulky ancillary ligand (2,2,6,6-tetramethylheptane-3,5-dione) was applied for the synthesis of Ir(iii) complexes (Ir-DHBA and Ir-F-DHBA) to minimize the intimate interactions between Ir(iii) molecules and consequently to reduce triplet-triplet annihilation and triplet-polaron annihilation. When the two Ir(iii) complexes were applied as dopants in organic light-emitting diode (OLED) devices, they both showed excellent electroluminescence (EL) performance. The device based on Ir-DHBA demonstrated a low efficiency roll-off with a maximum external quantum efficiency (EQE) of 26.0%, 25.3% EQE at a brightness of 1000 cd m-2 and 22.7% EQE at 10?000 cd m-2. The device based on Ir-F-DHBA (at a doping ratio of 3%) with an exciplex as a co-host showed a maximum EQE of over 28% with Commission Internationale de l'Eclairage (CIE) coordinates of (0.61, 0.39) and an EL emission peak at 600 nm.

Nickel-catalyzed α-alkylation of ketones with benzyl alcohols

We reported an efficient method for α-alkylation of ketones with benzyl alcohols using the pyridine-bridged pincer-type N-heterocyclic carbenes nickel complexes as catalysts. A wide range of ketones and benzyl alcohols were efficiently converted into various alkylated products in moderate to high yields. In addition, these nickel complexes were also successfully applied for the synthesis of a wide range of quinoline derivatives.

Pincerlike manganese complex and preparation method thereof, related ligand and preparation method thereof, catalyst composition and application

The invention discloses a pincerlike manganese complex, a preparation method thereof, a ligand for preparation, a preparation method of the ligand, a catalyst composition taking the complex as an active component and application of the catalyst composition. According to the pincerlike manganese complex, a cycloalkyl ring is introduced into a ligand framework, and by regulating and controlling the cyclic tension, flexibility and steric hindrance of the cycloalkyl ring, the reactivity and stability of the manganese metal center can be effectively adjusted, and the catalytic activity and substrate applicability of a manganese metal system are remarkably improved. The catalyst composition taking the pincerlike manganese complex as an active component has the advantages of high catalyst activity, wide substrate application range, mild reaction conditions and the like in the process of preparing quinoline or pyridine derivatives by catalyzing dehydrogenation coupling reaction of o-amino aromatic alcohol or gamma-amino alcohol, ketone or secondary alcohol; and the synthesis advantages of low cost and stable performance are embodied, the operation is simple, and the yield is high.

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

A simple and efficient ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolinesviaoxidative cyclization of oxime acetates with 2-aminobenzyl alcohols at room temperature has been developed. The presented approach provides a new synthetic pathway leading to polysubstituted quinolines with good functional group tolerance under mild conditions. Moreover, this transformation can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as the internal oxidants in the reactions, thus making this method very attractive.

Copper-catalyzed formal [3 + 3] annulations of arylketoximes and o-fluorobenzaldehydes: An entry to quinoline compounds

A copper-based catalytic system has been developed to enable efficient cyclization of ketoxime acetates with ofluorobenzaldehydes. This protocol offers an efficient method for the synthesis of substituted quinoline derivatives with a broad range of compatible functionalities. The present system also provides a rapid access to synthetically and pharmaceutically useful quinoline-fused polycycles such as benzo[c]acridines.

Visible-Light-Mediated Oxidative Cyclization of 2-Aminobenzyl Alcohols and Secondary Alcohols Enabled by an Organic Photocatalyst

This paper describes a visible-light-mediated oxidative cyclization of 2-aminobenzyl alcohols and secondary alcohols to produce quinolines at room temperature. This photocatalytic method employed anthraquinone as an organic small-molecule catalyst and DMSO as an oxidant. According to this present procedure, a series of quinolines were prepared in satisfactory yields.

Direct synthesis of ring-fused quinolines and pyridines catalyzed byNNHY-ligated manganese complexes (Y = NR2or SR)

Four cationic manganese(i) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (whereNNHis a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alcohol with a ketone or secondary alcohol;NNHS-ligatedMn-4proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and experimental evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclicN-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.