17286-62-3

Upstream product

• 4079-54-3 2-hydroxy-1-p-tolyl-ethanone 
• 95-54-5 1,2-diamino-benzene 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 518068-74-1 2,4-dinitro-benzenesulfonic acid 2-oxo-2-p-tolyl-ethyl ester 
• 98475-04-8 1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 1448-87-9 2-chloroquinoxaline 
• 14338-21-7 tri-(4-methylphenyl)aluminum 
• 4209-16-9 N-phenyl-1-(p-tolyl)ethan-1-imine 
• 62-53-3 aniline 
• 122-00-9 para-methylacetophenone 
• 97401-87-1 N-tosyl-2-(p-tolyl)aziridine 
• 615-36-1 2-bromoaniline 
• 3261-62-9 2-(p-tolyl)ethylamine 

Downstream Products

• 1221687-22-4 (R)-2-(p-tolyl)-1,2,3,4-tetrahydroquinoxaline 
• 1262801-85-3 2-(4-methyl-2-nitrophenyl)quinoxaline 
• 1327154-17-5 2-(p-tolyl)-1,2,3,4-tetrahydroquinoxaline 
• 1420295-57-3 2-(dimethoxymethyl)-3-p-tolylquinoxaline 
• 1253208-04-6 (S)-2-(p-tolyl)-1,2,3,4-tetrahydroquinoxaline 

Relevant academic research and scientific papers

Palladium-catalyzed cross-coupling of 2-chloroquinoxaline N-Oxides with arylboronic acids

A selection of 2-chloro-substituted O-alkylquinoxaline N-oxides, easily accessible by the one-step annulation reaction of 4-fluoroaniline with 1,1,2-trichloro-2-nitroethylene and subsequent O-alkylation, was arylated at the chloronitrone unit in yields up to 96 %. This first efficient Pd-catalyzed Suzuki-Miyaura reaction of chloroquinoxaline N-oxides with arylboronic acids led to new 2-arylquinoxaline N-oxides. The scope and limitations of this arylation reaction were investigated, and the role of some sterically demanding boronic acids in the cross-coupling reaction was evaluated by means of DFT calculations. Additionally, the Pd-catalyzed C-arylation of the amide unit of selected quinoxalinone derivatives was accomplished. For the first time the chloronitrone unit of 2-chloroquinoxaline N-oxides was arylated with arylboronic acids under Suzuki-Miyaura cross-coupling conditions in good to very good yields. The scope and limitations of the applied protocols were investigated as well as the dependency of the yield of the reaction on the steric bulk of the arylboronic acid by means of DFT calculations. Copyright

Manganese(IV) dioxide-catalyzed synthesis of quinoxalines under microwave irradiation

We synthesize quinoxalines, catalyzed by manganese(IV) dioxide, from a variety of α-hydroxyketones followed by trapping with aromatic or aliphatic 1,2-diamines without using a solvent, within one minute under microwave irradiation. The Royal Society of Chemistry 2005.

Silica nanosphere–graphene oxide (SiO2–GO) hybrid catalyzed facile synthesis of functionalized quinoxaline derivatives

Abstract: Herein, fabrication of spherical SiO2 nanoparticles (5?±?0.2?nm) with uniform size is followed by their homogeneous distribution on graphene oxide (SiO2–GO) by using a simple in situ one-step method. These as synthesized ca

Mechanically induced transition metal free C(sp2)-H arylation of quinoxalin(on)es with diaryliodonium salts and piezoelectric BaTiO3

A transition metal free mechanically induced C(sp2)-H arylation of quinoxalin(on)es is described. In this study, diaryliodonium salts generate aryl radical by planetary ball milling, with the assist of piezoelectric material BaTiO3. A broad range of functional groups are tolerated to give products in moderate to good yields via radical mechanism.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

Silica supported dodecatungstophosphoric acid (DTP/SiO2): An efficient and recyclable heterogeneous catalyst for rapid synthesis of quinoxalines

A facile synthesis of quinoxalines by the cyclocondensation of substituted phenacyl bromides with o-pheneylenediamines using silica-supported dodecatungstophosphoric acid (DTP/SiO2) as a recyclable heterogeneous catalyst is unveiled in this res

Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source

A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

N, C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions

Various monosubstitution and disubstitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied while looking for ways to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that (1) preactivation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with approximately half the loading of Pd, relative to that previously required based on a combination of a Pd(II) salt and ligand; and (3) the most effective palladacycle precatalyst has been identified as that containing an isopropyl group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion (P13). This precatalyst is also effective in other C-C bond-forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A one-pot, four-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this precatalyst to maximize synthetic gain while minimizing costs and waste generation.