7092-81-1

Usage

Uses

Used in Pharmaceutical Industry:
7,8,9,10-TETRAHYDRO-6H-CYCLOHEPTA[B]QUINOLINE is used as a starting material for the synthesis of various pharmaceutical compounds due to its potential pharmacological properties. Its antipsychotic and analgesic effects make it a promising candidate for the development of new drugs to treat mental disorders and pain management.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 7,8,9,10-TETRAHYDRO-6H-CYCLOHEPTA[B]QUINOLINE is utilized as a scaffold for designing and developing new drugs with improved therapeutic effects and reduced side effects. Its unique chemical structure allows researchers to modify and optimize its properties for specific medical applications.
Used in Drug Discovery:
7,8,9,10-TETRAHYDRO-6H-CYCLOHEPTA[B]QUINOLINE plays a crucial role in drug discovery, as its chemical properties and potential pharmacological effects make it an attractive target for the development of innovative therapeutic agents. Researchers can use 7,8,9,10-TETRAHYDRO-6H-CYCLOHEPTA[B]QUINOLINE to identify new drug targets and design drugs with enhanced efficacy and safety profiles.

Upstream product

• 577-19-5 2-nitrophenyl bromide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 502-41-0 cycloheptanol 
• 4403-69-4 2-amino-1-benzylamine 
• 502-42-1 cycloheptanone 
• 552-89-6 2-nitro-benzaldehyde 
• 85236-13-1 2-bromocyclohept-1-ene-1-carbaldehyde 
• 62-53-3 aniline 
• 13683-43-7 N-cycloheptylidenebenzenamine 
• 187964-68-7 N-(1H-1,2,3-benzotriazol-1-ylmethylene)-N-methylmethanaminium chloride 
• 66660-64-8 2-[1-Phenyl-meth-(E)-ylidene]-cycloheptanone oxime 
• 749250-23-5 (E)-2-(bromomethylidene)cycloheptanone 

Downstream Products

• 14788-49-9 (+/-)-5-benzoyl-(5ar,10at)-5a,6,7,8,9,10,10a,11-octahydro-5H-cyclohepta[b]quinoline 

Relevant academic research and scientific papers

Bis(imino)pyridines fused with 6- and 7-membered carbocylic rings as: N, N, N -scaffolds for cobalt ethylene polymerization catalysts

The unsymmetrical diketone, 1,2,3,7,8,9,10-heptahydrocyclohepta[b]quinoline-4,6-dione, based on a central pyridine unit fused by both 6- and 7-membered rings, has been synthesized via a sequence of reactions including ruthenium-catalyzed coupling cyclization. Templating this diketone with a mixture of cobalt(ii) chloride hexahydrate and the corresponding aniline in acetic acid at reflux afforded five examples of carbocyclic-fused bis(arylimino)pyridine-cobalt(ii) chlorides (aryl = 2,6-Me2Ph Co1, 2,6-Et2Ph Co2, 2,6-i-Pr2Ph Co3, 2,4,6-Me3Ph Co4, 4-Me-2,6-Et2Ph Co5) in good yield. All cobalt complexes have been fully characterized including by 1H NMR spectroscopy which reveals broad but assignable paramagnetically shifted peaks. The molecular structures of Co1, Co3 and Co4 highlight the inequivalency of the two fused rings with the cobalt center adopting a distorted trigonal bipyramidal geometry. Treatment of Co1-Co5 with MAO gave highly active catalysts (up to 5.03 × 106 g PE mol-1 (Co) h-1 at 40 °C, with Co4 > Co5 > Co1 > Co2 > Co3) for ethylene polymerization generating strictly linear vinyl-terminated polymers with low molecular weights (Mw range: 1.53-22.77 kg mol-1). By comparison, polymerizations conducted using Co1-Co5/MMAO were less active and displayed a lower selectivity for unsaturated polymers. Common to both MAO and MMAO, the most sterically hindered precatalyst Co3 gave the highest molecular weight polymer of the series (up to 22.77 kg mol-1) but exhibited the lowest activity.

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%.

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.

Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles

Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.

Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process

Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.

Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines

A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.

Synthesis of Pyridines, Quinolines, and Pyrimidines via Acceptorless Dehydrogenative Coupling Catalyzed by a Simple Bidentate P^ N Ligand Supported Ru Complex

A ruthenium hydrido chloride complex (1) supported by a simple, heteroleptic bidentate P^N ligand (L1) containing a diarylphosphine and a benzannulated phenanthridine donor arm is reported. In the presence of base, complex 1 catalyzes multicomponent reactions using alcohol precursors to produce structurally diverse molecules including pyridines, quinolines, and pyrimidines via acceptorless dehydrogenative coupling pathways. Notably, L1 does not bear readily (de)protonated Br?nsted acidic or basic groups common to transition metal catalysts capable of these sorts of transformations, suggesting metal-ligand cooperativity does not play a significant role in the catalytic reactivity of 1. A rare example of an η2-aldehyde adduct of ruthenium was isolated and structurally characterized, and its role in acceptorless dehydrogenative coupling reactions is discussed.

Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions

Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80 °C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alcohol/1-phenylethanol and diamine/diol, respectively, in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alcohol follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O2 oxidation makes this protocol eco-friendly and easy to handle.

Synthesis and Structures of Arene Ruthenium (II)–NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction

A panel of six new arene Ru (II)-NHC complexes 2a-f, (NHC?=?1,3-diethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1a, 1,3-dicyclohexylmethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1b and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1c) were synthesized from the transmetallation reaction of Ag-NHC with [(η6-arene)RuCl2]2 and characterized. The ruthenium (II)-NHC complexes 2a-f were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcohols as coupling partners respectively. The reactions were performed with 0.5?mol% catalyst load in 8?h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations.

Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex

The invention provides a pyridylimine group complex containing asymmetric fused rings and a preparation method and application of an intermediate of the pyridylimine group complex. The complex has high catalytic activity, can realize the regulation of the molecular weight of a polymer by changing a ligand structure and polymerization conditions, and has the advantages such as low cost and stable performance. The preparation method of the intermediate 2,3,7,8,9,10 hexahydro-1H-cycloheptaquinoline-4,6-dione compound and the complex has the advantages such as mild conditions, short cycle and simple operating conditions. The complex can be applied to a catalyst for ethylene polymerization, especially when an iron complex provided has high thermal stability, the catalytic activity can be as high as 15.86x10 g.mol(Fe)h under the action of a catalyst promoter MMAO, highly linear polyethylene is obtained, the catalytic activity can still be maintained at 5.44x10 g.mol(Fe)h even at a high temperature of 90 DEG C, the temperature is in line with the operating temperature of industrial production, and the pyridylimine group complex has good industrial application prospects.