30160-12-4

Upstream product

• 55857-35-7 (E)-N-(2-aminobenzylidene)-4-methylaniline 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 125105-18-2 o-nitrobenzylidene du benzoylacetate d'ethyle 
• 64-17-5 ethanol 
• 2819-08-1 benzoyl acetate 
• 55857-35-7 N-(2-aminobenzylidene)-4-methylaniline 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 623-47-2 propynoic acid ethyl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 53256-22-7 ethyl β-anilinocinnamate 
• 68-12-2 N,N-dimethyl-formamide 
• 4403-69-4 2-amino-1-benzylamine 
• 271-58-9 anthranil 

Downstream Products

• 113387-33-0 phenyl-2 carbethoxy-3 dihydro-1,2 quinoleine 
• 871022-77-4 3-(hydroxymethyl)-2-phenylquinoline 
• 871022-79-6 (2-phenylquinolin-3-yl)methanethiol 
• 871022-78-5 3-(thiomethyl)-S-acetyl-2-phenylquinoline 
• 871022-80-9 3-(thiomethyl)-S-(Boc-Gly)-2-phenylquinoline 
• 871022-82-1 3-(thiomethyl)-S-(D-Phe)-2-phenylquinoline 
• 871022-81-0 3-(thiomethyl)-S-(Boc-D-Phe)-2-phenylquinoline 
• 871022-83-2 3-(thiomethyl)-S-(Boc-Gly-D-Phe)-2-phenylquinoline 
• 94202-58-1 t-Boc-D-phenylalanyl-L-phenylalanine methyl ester 
• 1535966-39-2 (+)-ethyl 2-phenyl-1,2,3,4-tetrahydroquinoline-3-carboxylate 
• 142849-37-4 4-Carboethoxy-3-phenyl-2-azabicyclo[4.4.0]decane 

Relevant academic research and scientific papers

Rawal's catalyst as an effective stimulant for the highly asymmetric Michael addition of β-keto esters to functionally rich nitro-olefins

A general approach to asymmetric synthesis of highly substituted dihydroquinolines was achieved through neighboring ortho-amino group engaged sequential Michael/amination/dehydration reactions on (E)-2-(2-nitrovinyl)anilines with cyclic and acyclic β-keto esters in the presence of a catalytic amount of Rawal's quinidine-NH-benzyl squaramide followed by TFA.

NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.

Quinoline derivative as well as preparation method and application thereof

The invention belongs to the technical field of chemical drug synthesis, and particularly relates to a quinoline derivative as well as a preparation method and application thereof. In a reaction system, firstly, a metal catalyst, a ligand and a silicon hydrogen reagent interact to generate metal hydride, the metal hydride and an alkyne compound are subjected to addition, the metal hydride and an anthranil compound are subjected to an electrophilic amination reaction, and then the polysubstituted quinoline derivative is obtained through intramolecular cyclization. According to the invention, the starting raw materials such as the alkyne and the anthranil compound of the reaction are cheap and easily available, a variety of different polysubstituted quinoline derivatives can be constructed by using the one-step method, and can be rapidly converted into other compounds through the oxidation, the reduction, the coupling and other approaches of the target molecule so as to provide the good application prospect in the fields of drug development and material preparation; and the method is mild in condition, green, efficient, simple to operate and very suitable for large-scale industrial production.

Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst

An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.

An efficient heterogeneous gold(I)-catalyzed intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes leading to polyfunctionalized quinolines

The first heterogeneous intermolecular cycloaddition of 2-aminoaryl carbonyls and internal alkynes was realized in DMF at 100 °C by using a triphenylphosphine-functionalized MCM-41-supported gold(I) complex [MCM-41-PPh3-AuCl] and AgOTf as catal

Copper-Catalyzed Tandem Reaction of Enamino Esters with ortho-Halogenated Aromatic Carbonyls: One-Pot Approach to Functionalized Quinolines

An efficient and practical approach for the synthesis of functionalized quinolines has been developed by using the copper-catalyzed tandem C–C bond formation and C–N coupling reaction of enamino esters and ortho-halogenated aromatic carbonyl compounds. Various functional groups were tolerated under the reaction conditions, and a series of quinolines were easily obtained in moderate to good yields. A gram-scale reaction was also performed to demonstrate a further application of this synthetic method.

Palladium-Catalyzed Intermolecular Aerobic Annulation of o-Alkenylanilines and Alkynes for Quinoline Synthesis

A new approach to construct 2,3-disubstituted quinolines is described via Pd-catalyzed oxidative cyclization of o-vinylanilines and alkynes with molecular oxygen. This transformation is supposed to undergo intermolecular amination of alkyne, insertion of the olefin, and oxidative cleavage of C-C bond sequence.

An efficient synthesis of quinolines via copper-catalyzed C-N cleavage

An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su

FeCl3-promoted formation of C-C bonds: Synthesis of substituted quinolines from imines and electron-deficient alkynes

An efficient method for the synthesis of substituted quinolines is described. By FeCl3-promoted C-C bond formation, 2,3-disubstituted and 2,3,4-trisubstituted quinolines were successfully synthesized from the reaction between imines and electron-deficient alkynes in good yields. The reaction can also be performed in a sequential three-component manner by using aromatic amines and aromatic aldehydes instead of the corresponding imines.

An unexpected one-pot synthesis of multi-substituted quinolines via a cascade reaction of Michael/Staudinger/aza-Wittig/aromatization of ortho-azido-β-nitro-styrenes with various carbonyl compounds

Multi-substituted quinolines 3 were unexpectedly prepared from a cascade reaction of ortho-azido-β-nitro-styrenes with various carbonyl compounds. This method takes advantages of mild condition, simple work-up, high yield as well as wide substrate scope, which makes this method powerful for one-pot synthesis of multi-substituted quinolines.