30290-78-9

Upstream product

• 605-03-8 4-phenylquinoline 
• 64-17-5 ethanol 
• 4888-33-9 4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 100-42-5 styrene 
• 622-79-7 benzyl azide 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 890411-58-2 1,2-diphenylazetidine 
• 2983-48-4 1-phenyl-3-(phenylamino)propan-1-one 
• 3056-73-3 N-phenylcinnamamide 
• 14371-10-9 (E)-3-phenylpropenal 
• 92573-86-9 N-[(2E)-3-phenylprop-2-en-1-yl]aniline 
• 62-53-3 aniline 
• 102-92-1 Cinnamoyl chloride 

Downstream Products

• 27623-83-2 1-methyl-4-phenyl-1,2,3,4-tetrahydroquinoline 
• 111663-92-4 phenyl(4-phenyl-3,4-dihydroquinolin-1(2H)-yl)methanone 
• 76061-98-8 1-Cyanoacetyl-4-phenyl-1,2,3,4-tetrahydroquinoline 
• 76061-83-1 1-Guanidinoacetyl-4-phenyl-1,2,3,4-tetrahydroquinoline hydrochloride 
• 695143-00-1 1-Aminoacetyl-4-phenyl-1,2,3,4-tetrahydroquinoline 
• 605-03-8 4-phenylquinoline 
• 76061-90-0 1-Chloroacetyl-4-phenyl-1,2,3,4-tetrahydroquinoline 

Relevant academic research and scientific papers

Encapsulating Cobalt into N-Doping Hollow Frameworks for Efficient Cascade Catalysis

The development of nonprecious catalysts for hydrogenation of organic molecules is of great importance in heterogeneous catalysis. Herein, we report a series of N-doped hollow carbon frameworks encompassing cobalt nanoparticles (denoted as Co@NHF-900) constructed as a new kind of reusable catalyst for this purpose by pyrolysis of ZIF-8@Co-dopamine under Ar atmospheres. Notably, the framework of ZIF-8 is essential for efficient catalyst by providing a carbon framework to support Co-dopamine. The experimental results reveal that the ZIF-8 renders a large hollow place within the catalysts, allowing the enrichment of the substrate and windows of the hollow structure and the ease of mass transfer of products during the reaction. All of the virtues made Co@NHF-900 a good candidate for hydrogenation of quinolines with high activity (TOF value of 119 h-1, which is several times than that of akin catalysts) and chemoselectivity.

Cu Nanoclusters Anchored on the Metal-Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

Free-access active sites created and the interaction regulated between them and substrates during the heterogeneous catalysis process are crucial, which remain a great challenge. In this work, in suit reduced to afford naked Cu nanoparticles (NPs) have been anchored on the metal-organic framework (MOF), NH2-MOF, to form Cu-NH2-MOF. The strategy can precisely control the Cu NP formation with small size and uniform distribution. The Cu NP properties and MOF advantages have been integrated to create a great catalyst with multiple functions and have resulted in improving the recyclability and superb catalytic activity for the one-pot reduction of heterocycle reactions under mild conditions. The experimental and theoretical calculation results show that the superior performance should be attributed to the framework of NH2-MOF that provides large caves for substrate enrichment and the stabilization of Cu sites by the -NH2 group.

Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines

An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-Npropargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-metasubstituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions

A new class of co-catalytic system was developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular oxygen as a terminal oxidant. A variety of quinolines were efficiently synthesized by the developed Cu and di-tert-butyl azodicarboxylate co-catalytic system.

Simple and convenient approach for synthesis of tetrahydroquinoline derivatives and studies on aza-Cope rearrangement

A simple and novel synthesis of 1,2,3,4-tetrahydroquinoline derivatives by polyphosphoric acid-assisted reaction of N-aryl allyl anilines prepared from anilines has been reported. The generality and scope of the approach has been demonstrated by extending it to the synthesis of 1,2,5,6-tetrahydro-4H- pyrrolo[3,2,1-ij]quinoline (lilolidine) and 2,3,6,7-tetrahydro-1H,5H-pyrido[3,2, 1-ij]quinoline (julolidine). Further, Lewis acid- mediated aza-Cope rearrangement of various N-aryl allyl anilines has been demonstrated.

Photogeneration and reactivity of 1,n-diphenyl-1,n-azabiradicals

The 1,5-diphenyl-1,5-azapentanediyl biradical Ia was generated by photolysis of 1,2-diphenylazacyclopentane (pyrrolidine 1a). Among the reaction pathways followed by Ia, C-N bond reformation with ring closure was found to be the predominating process, as determined by separate irradiation of either of the pure enantiomers of 1a. Disproportionation was a minor process and took place only via H abstraction by the C5 benzylic radical. Another minor pathway was C5-aryl coupling, with formation of 5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b] azepine (4a), which is equivalent to photo-Claisen rearrangement of 1a. Likewise, the 1,4-diphenyl-1,4-azabutanediyl biradical Ib was generated by photolysis of 1,2-diphenylazacyclobutane (azetidine 1b). This species underwent predominating C2-C3 cleavage, as indicated by the extensive styrene formation. Although NI-C4 bond reformation also took place, this is not the major pathway occurring from Ib. Besides, C4-aryl coupling to give 4-phenyl-1,2,3,4- tetrahydroquinoline (4b) was also observed. All the possible reaction pathways were theoretically studied at the UB3LYP/6-31G* computational level; the results were found to be in good agreement with the experimental observations.

Reactions of azides with electrophiles: New methods for the generation of cationic 2-azabutadienes. Synthesis of 1,2,3,4-tetrahydroquinolines and 1,2-dihydroquinolines via a hetero Diels-Alder reaction

Two methods for the generation of iminium ions of the type ArN+(X)=CHR (X = H or alkyl, R = H or alkyl) are reported: (1) the Bronsted-acid-promoted rearrangement of benzylic azides and (2) the intermolecular Schmidt reactions of azides XN3 (X = aliphatic) with benzylic carbocations derived from benzylic alcohols ArCH(R)OH. The iminium ions ArN+(X)=CHR behave as cationic 2-azabutadienes in the presence of alkenes and alkynes, producing 1,2,3,4-tetrahydroquinolines and 1,2-dihydroquinolines by a hetero Diels-Alder reaction.