1208259-15-7

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 4403-69-4 2-amino-1-benzylamine 
• 50-00-0 formaldehyd 
• 1427216-57-6 (Z)-2-methyl-N'-phenylbenzimidamide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 529-19-1 2-Methylbenzonitrile 
• 527-85-5 o-Methylbenzamid 
• 577-16-2 2-Methylacetophenone 
• 100-46-9 benzylamine 
• 5021-43-2 2-phenylquinoxaline 
• 89-93-0 ortho-methylbenzylamine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 135436-97-4 (E)-2-nitrobenzaldehyde O-methyl oxime 

Downstream Products

• 1451359-67-3 (E)-4-styryl-2-(o-tolyl)quinazoline 

Relevant academic research and scientific papers

Synthesis of 2-aryl quinazolines from (2-aminophenyl)methanol and oxime ether catalyzed by copper ferrite nanoparticles

Magnetically separable copper ferrite nps as a catalytic system, under solvent free reaction condition for synthesis of 2-arylquinazolines has been reported. (2-aminoaryl)methanols and various types of oxime ethers were efficiently converted into desired products in moderate to good yields. This protocol offers a greener and atom efficient process, using recyclable heterogeneous catalytic system.

Rh(III)-catalyzed oxidative ortho -C-H alkylation of 2,4-diarylquinazoline with potassium alkyltrifluoroborates

Alkyltrifluoroborates were used for Rh(III)-catalyzed ortho-alkylation of 2,4-disubstituted quinazoline via C-H bond activation. The reaction proceeded well with a broad substrate scope, providing a direct way to access high functional quinazoline core structure derivatives in yields up to 95%.

Possible competitive modes of decarboxylation in the annulation reactions ofortho-substituted anilines and arylglyoxylates

Annulation reactions ofortho-substituted anilines and arylglyoxylates in the presence of K2S2O8at 80 °C under metal-free neutral conditions have been investigated, which extended a platform for the tandem synthesis of nitrogen heterocycles. While arylglyoxylic acids are known to undergo decarboxylation to form an acyl radical in the presence of K2S2O8and used in the Minisci acylation of electron-deficient (hetero)aromatics, their reactions with electron-richortho-substituted anilines to form nitrogen heterocycles have recently been studied. Depending upon the experimental conditions used in the reactions, the mechanism of the formation of heterocycles involving reactions of an acyl radical or aryl iminocarboxylic acids has been postulated. Given the subtle understanding of the mechanisms of annulation reactions of 2-substituted anilines and arylglyoxylates in the presence of K2S2O8, an extensive mechanistic investigation was undertaken. In the current study, the various mechanistic pathways including the generation of acyl, imidoyl, aminal, and N,O-hemiketal radicals have been postulated based on different possible decarboxylation modes. Some of the proposed intermediates are supported based on the available analytical data. The protocol uses a single, inexpensive reagent K2S2O8, which offers not only transition-metal-free conditions but also serves as the reagent for the key decarboxylation step. Taken together, this study complements the current development of the annulation reactions of 2-substituted anilines and arylglyoxylates in terms of synthesis and mechanistic understanding.

Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides

The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.

A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds

The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr

Ruthenium complex and preparation method thereof and catalytic application

The invention discloses a ruthenium complex and a preparation method thereof and catalytic application. The ruthenium complex is reported for the first time. Research finds that the ruthenium complexhas the activity of catalytically synthesizing quinazoline and derivatives thereof or catalytically synthesizing quinoline and derivatives thereof. When the ruthenium complex provided by the inventionis used for catalytic synthesis of quinazoline and derivatives thereof or quinoline and derivatives thereof, the ruthenium complex has the advantages of mild reaction conditions, wide substrate range, high catalytic product yield and good functional group tolerance, and is significantly superior to the prior art.

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.

Mixed crystalline phases and catalytic performance of OMS-2 based nanocomposites for one-pot synthesis of quinazolines with O2 as an oxidant

In this work, a series of sodium phosphotungstate modified manganese oxide octahedral molecular sieve (OMS-2) catalysts ([PW]-OMS-2) were developed, and their catalytic activities were investigated by one-pot synthesis of quinazolines from benzyl alcohol and 2-aminobenzylamine with O2 as green oxidant in dimethyl carbonate (DMC). TEM, XRD and EDS confirmed that sodium phosphotungstate decomposed into phosphotungstic acid and sodium tungstate in the doping process. Meanwhile, phosphotungstic acid attached and located at the surface of OMS-2 and W ions were successfully doped into the OMS-2 framework. For comparison, phosphotungstic acid/OMS-2 was prepared by simple wet impregnation method. The [PW]-OMS-2 is the most highly selective and effective over than phosphotungstic acid/OMS-2 and OMS-2 itself in the one-pot synthesis of quinazolines. It may be due to the synergetic effect of phosphotungstic acid and OMS-2, and successfully doping W into OMS-2 frameworks. Hence, this work provides a new environmentally-friendly and heterogeneous OMS-2 based nanocomposites and it may be put into practice to synthesize heterocyclic compounds.

Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach

Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.

Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation

Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.