198068-91-6

Upstream product

• 28144-70-9 anthranilic acid amide 
• 591-31-1 3-methoxy-benzaldehyde 
• 612-24-8 o-nitrobenzonitrile 
• 118-48-9 isatoic anhydride 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 56071-04-6 3'-methoxy-2-phenyl-4-quinazolinone 
• 1217862-32-2 C₁₅H₁₄N₄O 
• 1448069-14-4 2-(3-methoxyphenyl)-3,4-dihydroquinazolin-4-thione 
• 56071-04-6 2-(3-methoxyphenyl)quinazolin-4(3H)-one 
• 1448068-54-9 C₁₆H₁₃N₅O 

Relevant academic research and scientific papers

Facile and efficient protocols for C–C and C–N bond formation reactions using a superparamagnetic palladium complex as reusable catalyst

Abstract: Facile and efficient protocols for some multicomponent coupling reactions such as the Suzuki reaction and synthesis of polyhydroquinoline and 2,3-dihydroquinazoline-4-(1H)-one derivatives using a superparamagnetic palladium complex as catalyst have been developed. Graphical abstract: [Figure not available: see fulltext.].

Copper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol-Water

A copper-catalyzed one-pot synthesis of 2,3-dihydroquinazolin-4(1 H)-ones with diboronic acid as a reductant in an aqueous medium is described. Various 2,3-dihydroquinazolin-4(1 H)-ones were prepared with good functional-group tolerance in good yields under mild conditions from readily available 2-nitrobenzonitriles and various carbonyl compounds.

A Facile Microwave and SnCl2Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones

An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17-99 %. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels-Alder addition. As a result, thiophene afforded high yields (80 %) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.

Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

CoFe2O4@SiO2-CPTES-Guanidine-Cu(II): A novel and reusable nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines and oxidation of sulfides

CoFe2O4@SiO2-CPTES-Guanidine-Cu(II) magnetic nanoparticles were synthesized and used as a new, inexpensive and efficient heterogeneous catalyst for the synthesis of polyhydroquinolines and 2,3-dihydroquinazoline-4(1H)-ones and for the oxidation of sulfides. The structure of this nanocatalyst was characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, X-ray diffraction and inductively coupled plasma optical emission spectrometry. Simple preparation, high catalytic activity, simple operation, high yields, use of green solvents, easy magnetic separation and reusability of the catalyst are some of the advantages of this protocol.

Dihydroquinoxalinone compound and preparation method thereof

The invention relates to a dihydroquinoxalinone compound and a preparation method, and the specific structure is shown in III. The method uses cheap and readily available o-nitrobenzonitrile (I) and aldehyde or ketone (II) as raw materials, and alcohol and water as solvent. The target product (III) is obtained by a nitro reduction, a cyano hydrolysis, and a condensation reaction in a one-pot reaction system under the action of tetrahydroxydiboron, glacial acetic acid and catalytic amount of cuprous chloride. The preparation method uses 2-nitrobenzonitrile (I) as a raw material for the first time, which is easy to operate, easy to obtain raw materials, high in yield, and has the advantages of green synthesis such as step economy, atomic economy, mild reaction conditions and the like. The specific formula is shown in the description.

Synthesis and characterization of bromine source immobilized on diethylenetriamine-functionalized magnetic nanoparticles: A novel, versatile and highly efficient reusable catalyst for organic synthesis

Bromine source immobilized on magnetic nanoparticles functionalized with diethylenetriamine was successfully synthesized and characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, vibrating sample magnetometry, thermogravimetric analysis and X-ray diffraction. The catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives and in Knoevenagel condensation was studied. The bromine catalyst can be magnetically recovered and reused several times without significant loss of its catalytic activity. All products were obtained in high to excellent yields.

Synthesis and characterization of bromine source supported on magnetic Fe3O4 nanoparticles: A new, versatile and efficient magnetically separable catalyst for organic synthesis

Tribenzylammonium tribromide supported onto magnetic nanoparticles (Br3-TBA-Fe3O4) as a bromine source was successfully synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy and vibrating sample magnetometry. The synthesized catalyst is shown to be a versatile and highly efficient heterogeneous catalyst for the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-one and polyhydroquinoline derivatives. To the best of the authors' knowledge, this is the first report of the use of a bromine source immobilized on Fe3O4 nanoparticles as a magnetically separable catalyst for these reactions. The nanosolid catalyst can be magnetically recovered and reused readily several times without significant loss in catalytic efficiency.

Magnetic Fe3O4 nanoparticles supported amine: a new, sustainable and environmentally benign catalyst for condensation reactions

Abstract: Diethylenetriamine immobilized on magnetic Fe3O4 nanoparticles (DETA-Fe3O4) was successfully prepared as a new and well dispersed magnetically separable amine catalyst. The structure of the resulting catalyst was well characterized by a series of analysis techniques such as FT-IR, SEM, EDX, VSM, TGA and XRD. The catalytic activity of DETA-Fe3O4 was evaluated with Knoevenagel condensation of active methylene compounds with aromatic aldehydes. Interestingly, the cyclocondensation of anthranilamide and aldehydes were effectively catalyzed by DETA-Fe3O4 in water, and the desired products (2,3-dihydroquinazoline-4(1H)-ones) were afforded in admirable yields. Catalysis research under aqueous medium (water) also makes this synthetic protocol ideal and fascinating from the environmental point of view. The amine catalyst can be magnetically recovered after the reaction and can be reused many times without appreciable decrease in activity.

Sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives

The invention discloses a sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives. The dihydro-quinazolinone and quinazolinone derivatives are controllably prepared through a cascade reaction of anthranilamide or derivatives thereof and an aldehyde compound by taking sulfonic acid ionic liquid as a catalyst. Under the set catalytic reaction condition, the conversion rate of raw materials reaches up to 99%, and the yield of dihydro-quinazolinone and the yield of quinazolinone both can reach 95%. Compared with the prior art, the green solvent-ionic liquid is taken as the catalyst, no additional oxidizing agent or heavy metal catalyst is needed, the advantages that the reaction conditions are mild, environmental friendliness is achieved, the reaction selectivity and the product yield are high, controllable synthesis is achieved, and the catalyst can be recycled and reused conveniently are achieved, and the novel method is friendly to environment and efficient in synthesis.