4765-54-2

Upstream product

• 123-72-8 butyraldehyde 
• 28144-70-9 anthranilic acid amide 
• 88-67-5 2-Iodobenzoic acid 
• 3020-81-3 butylamidine hydrochloride 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 610-96-8 methyl chlorobenzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 7529-21-7 tributylamine N-oxide 
• 102-82-9 tributyl-amine 
• 71-36-3 butan-1-ol 
• 123-73-9 crotonaldehyde 
• 187737-37-7 propene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 84312-82-3 N-[2-(1-Hydroxy-1-methyl-ethyl)-phenyl]-butyramide 
• 84312-84-5 2-(β-Ethylstyryl)-4(3H)-quinazolinone 
• 84312-83-4 N-[2-(Hydroxy-diphenyl-methyl)-phenyl]-butyramide 
• 137416-69-4 2-Propyl-3-[[2'-(N-trityltetrazol-5-yl) biphenyl-4-yl]methyl]-4(3H)-quinazolinone 
• 96547-01-2 5-(2-Propyl-quinazolin-4-yloxymethyl)-3-(4-p-tolyl-piperazin-1-ylmethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 96547-00-1 3-(4-Phenyl-piperazin-1-ylmethyl)-5-(2-propyl-quinazolin-4-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 96547-12-5 C₂₁H₂₃N₅O₃S 
• 96547-22-7 (4-Methoxy-phenyl)-[5-(2-propyl-quinazolin-4-yloxymethyl)-[1,3,4]thiadiazol-2-yl]-amine 
• 96547-13-6 C₂₀H₂₀ClN₅O₂S 
• 96546-97-3 3-Morpholin-4-ylmethyl-5-(2-propyl-quinazolin-4-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 96547-11-4 C₂₁H₂₃N₅O₂S 
• 96547-23-8 (4-Chloro-phenyl)-[5-(2-propyl-quinazolin-4-yloxymethyl)-[1,3,4]thiadiazol-2-yl]-amine 
• 96546-98-4 3-Piperidin-1-ylmethyl-5-(2-propyl-quinazolin-4-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 96547-21-6 [5-(2-Propyl-quinazolin-4-yloxymethyl)-[1,3,4]thiadiazol-2-yl]-p-tolyl-amine 

Relevant academic research and scientific papers

Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions

A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.

Effect of Fe(iii)-based MOFs on the catalytic efficiency of the tandem cyclooxidative reaction between 2-aminobenzamide and alcohols

The catalytic properties of metal-organic frameworks (MOFs) containing triangular Fe(iii) clusters in the promotion of organic syntheses and photocatalysis applications have been receiving substantial attention for decades. These clusters are appealing due to the strong Lewis acidity afforded by coordinatively unsaturated sites upon the removal of solvent from the framework. In this paper, triangular Fe(iii) cluster-based MOFs were shown to be highly efficient heterogeneous catalysts for the solvent-free one-pot condensation of 2-aminobenzamide and alcohols to form quinazolin-4-ones under microwave irradiation. The Fe-MOF catalysts ranging from microporous to mesoporous structures with a variety of geometrical pore structures were investigated. Because of the open accessible spaces for reactants and high density of active sites, MOF-907, built from trimer Fe clusters and a mixture of two linkers, was more effective than other Fe(iii)-MOFs. The catalyst can be used for a broad substrate scope and recycled several times without a significant drop-off in its activity.

Commercial Copper-Catalyzed Aerobic Oxidative Synthesis of Quinazolinones from 2-Aminobenzamide and Methanol

The focus of this study was the development of a new synthetic method for quinazolinones based on the principles of Green Chemistry. Quinazolinones were synthesized from 2-aminobenzamide using methanol as both the C1 source and a green solvent in the presence of base Cs2CO3. Additionally, a commercially available, economical copper complex was used as a catalyst in the reaction. The desired products were achieved in moderate to high yield with up to 99 % isolated yield.

Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives

Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.

Method for preparing quinazolinone from enol

The invention discloses a method for preparing a quinazolinone derivative from enol. According to the method, a relatively inexpensive ruthenium complex is used as a catalyst in a reaction to catalyzea microwave reaction of commercial and easily-available 2-aminobenzamide with enol for the preparation of quinazolinone. Compared with conventional synthesis methods for quinazolinone of the same kind, the method of the invention has the following advantages: no alkali is used in the reaction process; clean and non-toxic tetrahydrofuran is used as a reaction solvent; hydrogen is automatically transferred, and the atom economy of the reaction is high; and the by-product of the invention is only water.

Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl

Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

Performing any synthesis using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the orthoposition, successful chemical reactions could be performed due to intramolecular control. At maximum contact of the reacting substances, i.e., under solvent-free mechanochemical conditions, 2-aminobenzamides, aryl-, alkylaldehydes and the iodine(V) reagent o-iodoxybenzoic acid (IBX) led to substituted quinazolin-4(3H)-one derivatives in fair yields.

The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru-clusters/Ceria Catalyst

Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru-clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H2O is generated as the only by-product. A series of quinazolinones with aromatic or non-aromatic substituents can be obtained in yields of up to 99 %. The Ru-clusters/ceria can be reused at least four times. The analysis of the E-factor (environmental impact factor) for the synthesis of 2-ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.

Quinazolinone compound preparation method

The present invention relates to a quinazolinone compound preparation method, wherein a quinazolinone-based compound is prepared by using 2-aminobenzamide, olefin and carbon monoxide as reaction substrates and using tetrahydrofuran as a solvent under the catalysis effect of a ruthenium loaded metal oxide. The reaction process comprises: adding tetrahydrofuran, 2-aminobenzamide, olefin and a catalyst into a pressure container, inflating with carbon monoxide, sealing, stirring, and carrying out a reaction for not less than 0.5 h at a reaction temperature of not lower than 120 DEG C, wherein thecatalyst is easily separated from the reaction system after the reaction, and can be recycled multiple times, and the yield of the quinazolinone-based compound is up to 100%.

Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues

A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.