73402-93-4

Upstream product

• 39859-36-4 2-amino-5-bromobenzophenone 
• 98-86-2 acetophenone 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 106-40-1 4-bromo-aniline 
• 100-42-5 styrene 
• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 189252-18-4 1-phenyl-1-(2-amino-5-bromophenyl)ethylene 
• 3412-44-0 1,3-diphenylpropene 
• 98-80-6 phenylboronic acid 
• 28383-65-5 ethyl 2-diazo-3-oxo-3-phenylpropanoate 
• 7702-38-7 N-(4-bromophenyl)benzamide 
• 2879-83-6 N-benzyl-N-(4-bromophenyl)amine 
• 780-20-1 N-benzylidene-4-bromoaniline 

Downstream Products

• 911383-08-9 Ir(acetylacetonato)(6-bromo-2,4-diphenylquinoline(-1H))2 

Relevant academic research and scientific papers

An aza-Diels-Alder route to polyquinolines

Polyquinolines have been studied since the early 1970s due to their favorable chemical, optical, electrical, and mechanical properties. However, surprisingly few synthetic strategies have been developed for the preparation of these polymers. Herein, we demonstrate the application of the aza-Diels-Alder (Povarov) reaction for the synthesis of soluble polyquinolines from a bifunctional monomer. Our approach furnishes polyquinolines with a unique architecture and connectivity in only two synthetic steps from inexpensive, commercially available reagents. The reported strategy may therefore represent a welcome addition to the polymer chemist's toolkit by providing ready access to a diverse library of polyquinoline-type materials.

Tuning the saturated red emission: Synthesis, electrochemistry and photophysics of 2-arylquinoline based iridium(iii) complexes and their application in OLEDs

A series of novel iridium(iii) complexes with two 2-arylquinoline derivatives as cyclometalated ligands and one monoanionic ligand, such as acetylacetonate (acac), N,N′-diethyldithiocarbamate (Et2dtc) and O,O′-diethyldithiophosphate (Et2dtp), as ancillary ligands have been synthesized and structurally characterized by 1H NMR, MS and elemental analysis (EA). The cyclic voltammetry, absorption, emission and electroluminescence properties of these complexes were systematically investigated. Through extending π-conjugation, introducing electron-donating groups in the ligand frame, or changing the ancillary ligands, the HOMO energy levels of the iridium(iii) complexes can be tuned, while their LUMO levels remain little affected; in consequence, the emission wavelengths of the iridium(iii) complexes can be tuned in the range 606-653 nm. The highly efficient organic light-emitting diodes (OLEDs) with saturated red emission have been demonstrated. A maximum current efficiency of 10.79 cd A-1, at a current density of 0.74 mA cm-2, with an emission wavelength of 616 nm and Commisioon Internationale de L'Eclairage (CIE) coordinates of (0.65, 0.35), which are very close to the National Television System Comittee (NSTC) standard red emission, have been achieved when using complex (DPQ) 2Ir(acac) as a phosphor dopant. The Royal Society of Chemistry 2006.

Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO3 was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ? induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.).

MOF-5 as a highly efficient and recyclable catalyst for one pot synthesis of 2,4-disubstituted quinoline derivatives

A MOF-5-catalyzed three-component coupling reaction was developed as an efficient approach for the synthesis of 2,4-disubstituted quinoline derivatives via a one pot three-component reaction of aromatic amines, aldehydes and alkynes with excellent yields. The easy recovery and reusability of the catalyst, broad substrate scope, short reaction time, high yields of products and solvent-free conditions make this protocol practical, environmentally friendly and economically attractive.

Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Br?nsted acidic ionic liquid

Abstract: Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product. Graphic abstract: [Figure not available: see fulltext.].

Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction

An oxidative annulation for the synthesis of 2,4-diarylquinolines from o -allylanilines is disclosed that uses recyclable reagent Chloranil as the oxidant. The corresponding products are obtained in moderate to excellent yields. Furthermore, a one-pot access to 2,4-di aryl quinolines from easily available anilines and 1,3-diarylpropenes is described as a highly atom-efficient protocol that involves oxidative coupling, rearrangement, and oxidative annulation.

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

Quinoline compound and synthesis method thereof

The invention discloses a synthesis method of a quinoline compound. The synthesis method comprises the following steps: adding a diazocarbonyl compound and a 2-vinylaniline compound into a solvent, carrying out a reaction under the protection of an inert

Triazole-gold (TAAu) catalyzed three-component coupling (A3 reaction) towards the synthesis of 2, 4-disubstituted quinoline derivatives

A gold-catalyzed three-component coupling reaction (A3 reaction) was developed as an efficient approach for the synthesis of challenging 2, 4-disubstituted quinoline derivatives. Compared to previously reported Cu/Au bi-catalyst system, this protocol enables achieving A3 reaction only in the presence of triazole-gold catalyst. Notably, 4-alkyl substituted or 2-alkyl substituted quinoline derivatives were obtained with good yields, which highlighted the unique advantage of this new strategy.