612-96-4

Usage

Preparation

Synthesis of 2-phenylquinoline: Quinoline (1.0 g, 7.742 mmol) and phenyl lithium (2.30 mL, 2 M, 23.22 mmol) were reacted according to general procedure. Purification of the residue by silica gel column chromatography (EtOAc:MeOH:Et3N; 10-30:1:1 or PhMe:MeOH:Et3N; 10:1:1) gave 2-phenylquinoline (0.66 g, 42%) as an orange solid.Aniline (0.140 g, 1.50 mmol) and cinnamaldehyde (0.132 g, 1.00 mmol) were dissolved in toluene in a reaction vial equipped with a magnetic stirrer bar, followed by the addition of K10 (0.50 g). The reaction mixture was heated at a temperature of 110 ?C for 3 hours. After completion of the reaction, the crude product was purified by column chromatography over silica gel eluting with a mixture of Hexane : Ethyl acetate (20:1) to produce 2-Phenylquinoline as a yellow solid (0.044 g, 21%); (m.p. 82-84 ?C) (lit. 84-85 °C); Rf 0.67 (20:1 hexane:ethyl acetate);1H NMR (400 MHz, CDCl3) δH 7.46-7.51 (1H, m, H-4’), 7.53-7.56 (3H, m, H-6, 3’, 5’), 7.73- 7.77 (1H, m, H-7), 7.85 (1H, d, J = 8.31 Hz, H-5), 7.88-7.91 (1H, d, J = 8.31 Hz, H-3), 8.18- 8.27 (4H, m, H-4, 8, 2’, 6’)13C NMR(400 MHz, CDCl3) δC 119.2 (C-3), 126.7 (C-6), 127.2 (C-4a), 127.5 (C-2’, 6’), 127.9 (C-5), 128.4 (C-3’, 5’), 128.7 (C-4’), 128.9 (C-7, 8), 129.8 (C-4), 130.3 (C-1’), 137.9 (C-8a), 157.2 (C-2)

Synthesis Reference(s)

Synthetic Communications, 23, p. 1959, 1993 DOI: 10.1080/00397919308009854Chemical and Pharmaceutical Bulletin, 26, p. 3485, 1978 DOI: 10.1248/cpb.26.3485Journal of the American Chemical Society, 71, p. 2327, 1949 DOI: 10.1021/ja01175a017

InChI:InChI=1/C15H11N/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H

Upstream product

• 123-91-1 1,4-dioxane 
• 91-22-5 quinoline 
• 60-29-7 diethyl ether 
• 110-86-1 pyridine 
• 108-86-1 bromobenzene 
• 612-62-4 2-Chloroquinoline 
• 101096-74-6 2-phenylquinoline 
• 1144-20-3 2-phenyl-4-quinolinol 
• 501680-65-5 2-p-tolylsulfanylquinoline 
• 591-51-5 phenyllithium 
• 953-21-9 N-(3-phenylallylidene)benzenamine 
• 14752-72-8 1,N-Diphenylpropanimine 
• 13180-36-4 4-hydroxy-2-phenylquinoline-3-carboxylic acid ethyl ester 
• 37056-75-0 cinnamaldehyde-(N-phenyl oxime ) 

Downstream Products

• 5659-33-6 2-phenylquinoline 1-oxide 
• 2973-26-4 2-phenyl-4-quinolinecarbonitrile 
• 24005-23-0 2-phenyl-1,2,3,4-tetrahydroquinoline 
• 55570-28-0 2,2-Diphenyl-1,2-dihydrochinolin 
• 14886-84-1 N-methyl-2-phenylquinolium iodide 
• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 1570-04-3 2-phenyl-5,6,7,8-tetrahydroquinoline 
• 123629-22-1 (RS)-2-cyclohexyl-1,2,3,4-tetrahydroquinoline 
• 5855-52-7 2-phenylquinolin-4-amine 
• 64388-07-4 2‐(3‐nitrophenyl)quinoline 
• 64388-23-4 2-(4-nitrophenyl)quinoline 
• 243-68-5 benzo[4,5]thieno[3,2-b]quinoline 
• 136949-24-1 2-perfluorohexyl-2-phenyl-1,2-dihydroquinoline 
• 119408-45-6 2-(quinolin-2-yl)phenyltellurium(IV) tribromide 

Relevant academic research and scientific papers

Substrate-Tuned Domino Annulation for Selective Synthesis of Poly-substituted Benzo[ f]imidazo[2,1- a][2,7]naphthyridines and 3-Azaheterocyclic Substituted 2-Arylquinolines

A domino annulation/oxidation of heterocyclic ketene aminals (HKAs) and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. These reactions proceed well under mild conditions without any additives. Plausible mechanisms for such a polycyclic ring system assembly were also proposed. Moreover, benzo[f]imidazo[2,1-a][2,7]naphthyridine 3g displayed a fluorescence effect, demonstrating the potential applications in organic optical materials.

Furfuryl vinyl ethers in [4+2]-cycloaddition reactions

For the first time [4+2]-cycloaddition reactions were carried out between furfuryl vinyl ethers and typical dienophiles and heterodienes proceeding in uncatalyzed conditions and resulting in previously unknown heterocyclic systems containing either free v

Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes

Enantioselective [3 + 2] annulation of N-heteroarenes with alkynes has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand and reducing reagent. A variety of electron-deficient N-heteroarenes, including qui

Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents

The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline

A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).

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.

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.