1157-63-7

Upstream product

• 1882-71-9 2-amino-5-methoxybenzamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 6298-96-0 1-(4-methoxyphenyl)ethanamine 
• 99848-43-8 2-bromo-5-methoxybenzamide 
• 874-90-8 4-methoxybenzonitrile 
• 2393-23-9 4-methoxy-benzylamine 
• 54413-93-3 2-iodo-5-methoxybenzoic acid 
• 51721-68-7 4-methoxybenzamidine hydrochloride 
• 138642-47-4 2-bromo-5-methoxybenzonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 911469-36-8 4-(6-acetoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenyl acetate 

Relevant academic research and scientific papers

Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamide with benzonitriles in PEG

A simple and efficient Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamides with benzonitrile in PEG under metal and ligand‐free condition. All substituted benzonitriles were also well participated with the formation of the corresponding products in moderate to good yields.

Method for photocatalytic synthesis of quinazolinone compound in aqueous phase (by machine translation)

The method comprises the following steps: taking the compound of the formula (I) and the compound of the formula (II) as a solvent, adding a photocatalyst and a phase transfer catalyst to obtain the quinazolinone compound (III) under the condition of alkali and visible light. Compared with the prior art, the method not only can be applied to a large amount of functional groups, has high yield, few byproducts, and is simple and safe to operate, low in cost and environment-friendly. Wherein R is hydrogen or R1 Is H, C1 - C4 alkoxy, halogen or nitro; R2 Is H, substituted or unsubstituted phenyl, 2 - pyridyl or 2 - thienyl; the substituted phenyl is phenyl substituted by amino, nitro, C1 - C4 alkyl or C1 - C4 alkoxy. (by machine translation)

Method for synthesizing quinazolinone compound by photo-catalyzing alcohol oxidation in water phase

The invention discloses a method for synthesizing a quinazolinone compound by photo-catalyzing alcohol oxidation in a water phase, which comprises the following steps: by taking a compound shown as aformula (I) and a compound shown as a formula (II) as raw materials and water as a solvent, adding a visible light catalyst, and reacting under the conditions of alkali and visible light to obtain a quinazolinone compound (III). The method for preparing the quinazolinone compound is environmentally friendly, easy and convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applicable to a large number of functional groups, high in yield, few in byproducts, simple and safe to operate, low in cost and environment-friendly; wherein R1 is H, C1-C4 alkoxy, halogen or nitro; and R2 is H, substituted or unsubstituted phenyl, 2-pyridyl, 2-thienyl or 5-methylfuryl.

A practical synthesis of quinazolinones via intermolecular cyclization between 2-halobenzamides and benzylamines catalyzed by copper(I) immobilized on MCM-41

The heterogeneous tandem N-arylation/oxidative C–H amidation of 2-halobenzamides and benzylamines was achieved in DMSO at 110 or 120 °C by using an MCM-41-immobilized L-proline copper(I) complex [MCM-41-L-Proline-CuBr] as the catalyst and air as the oxidant, yielding a variety of quinazolinone derivatives in good yields. The new MCM-41-L-Proline-CuBr catalyst can easily be prepared from commercially readily available and inexpensive reagents and recovered by filtration of the reaction mixture, and reused up to seven times with almost consistent activity.

Efficient and selective microwave-assisted copper-catalyzed synthesis of quinazolinone derivatives in aqueous

Microwave-assisted copper-catalyzed cascade reactions between 2-halobenzoic acids and amidines to synthesize quinazolinone derivatives in water are reported. A variety of target products were obtained in good to excellent yields up to 94%. Its application was performed by the synthesis of 4-(1H-benzo[d]imidazol-2-ylthio)-6-methoxypteridine, which displayed significant anti-proliferation effect.

“On-water” synthesis of quinazolinones and dihydroquinazolinones starting from O-bromobenzonitrile

A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones

The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N-dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc)2] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent yields. The new heterogeneous palladium catalyst can easily be prepared by a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution, and recycled up to eight times without significant loss of activity.

Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions

The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.

One-Pot Copper(I)-Catalyzed Ligand/Base-Free Tandem Cyclooxidative Synthesis of Quinazolinones

A novel and efficient Cu(I)-catalyzed ligand- and base-free multipathway domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-bromobenzamide and multiform substrates such as aldehydes, alcohols, and methyl arenes for a one-pot protocol, whereas TMSN3 is used as a nitrogen source. A wide range of substrate scope, functional group tolerance, and operational simplicity are synthetically useful features.

Copper-catalyzed domino reaction involving C-C bond cleavage to construct 2-aryl quinazolinones

A copper-catalyzed approach for the synthesis of 2-aryl-quinazolinones through a domino reaction involving C-C bond cleavage is described. This protocol involves intramolecular C-C bond cleavage to construct 2-aryl-quinazolinones, which may offer an alternative method to prepare medically important quinazolinone derivatives and a new strategy for C-C bond cleavage. Besides C-C bond cleavage, this domino reaction includes N-arylation and benzylic C-H amidation. A copper-catalyzed approach for the synthesis of 2-aryl-quinazolinones through a domino reaction involving C-C bond cleavage is described. This transformation offers an alternative method to prepare medically important quinazolinone derivatives and a new strategy for C-C bond cleavage. Copyright