74375-08-9

Upstream product

• 74375-13-6 2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-N-methyl-benzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 4141-08-6 2-Amino-N-methylbenzamid 
• 118-48-9 isatoic anhydride 
• 74-89-5 methylamine 

Downstream Products

• 74375-17-0 2-(4-chloro-phenyl)-3-methylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

One-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones by Fe3O4@SiO2-imid-PMAn nano-catalyst under ultrasonic irradiation and reflux conditions

Abstract: Fe3O4@SiO2-imid-PMAn efficiently catalyzes the condensation reaction of isatoic anhydride, aldehydes, and primary amines or ammonium salts to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives under ultrasonic irradiation or reflux conditions. This method gives notable advantages such as operational simplicity, excellent yields, short reaction times, and absence of any tedious workup or purification. In addition, the excellent catalytic performance and the easy preparation, thermal stability, and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the aforementioned nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least six times without noticeable deterioration in catalytic activity and reaction yield. Graphical abstract: [Figure not available: see fulltext.]

Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Mechanochemical treatment of N-unsubstituted or N-methyl anthranilamide with benzaldehyde yielded their Schiff bases derivatives which could be easily cyclized to the corresponding 2-phenyl-2,3-dihydroquinazolinones via thermal rearrangement in water. On the basis of the above findings, an eco-friendly method was applied to prepare quinazolin-4(1H)-one derivatives from anthranilamides and a number of (hetero)aryl aldehydes. Heating the aqueous mixture of starting compounds to 90 °C resulted in the products in 81-94% yields. All products precipitated from the reaction mixture and were isolated by simply filtration. No further work-up or purification was necessary.

Efficient synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-ones catalyzed by dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation

Synthesis of 2,3-disubstituted-2,3-dihydroquinazolin-4(1H)-one derivatives catalyzed by dodecylbenzenesulfonic acid was carried out in 80-92% yields at 40-42 °C within 1-2 h in aqueous media via one-pot three-component condensation of isatoic anhydride, aromatic aldehyde and amine under ultrasound irradiation. Convenient work-up procedures, mild reaction conditions, avoiding the use of organic solvents, and friendly to environment are the salient features of this protocol.

Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using copper benzenesulfonate as a reusable catalyst in aqueous solution

Copper benzenesulfonate was found to be an effective catalyst for one-pot three-component cyclocon-densation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines in aqueous solution to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields. The catalyst is reusable and could be recycled for several times without distinct decrease in its efficiency. Springer-Verlag 2011.

Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using aluminum methanesulfonate as a reusable catalyst

A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed. Springer Science+Business Media B.V. 2011.

One-pot, three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones using p-Toluenesulfonic acid-paraformaldehyde copolymer as an efficient and reusable catalyst

p-Toluenesulfonic acid-paraformaldehyde copolymer (copolymer-PTSA) catalyzes the three-component, one-pot condensation reaction of isatoic anhydride, ammonium salts or aromaticand aliphatic amines, and aldehydes in refluxing ethanol. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Springer-Verlag 2010.

Ionic liquid promoted eco-friendly and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones

2,3-Dihydroquinazolin-4(1H)-ones were efficiently synthesised by the reaction of isatoic anhydride, a primary amine or ammonium acetate, and different aromatic aldehydes in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) without using any acidic catalyst. Also a bis-derivative of the title compound as a polyheterocyclic system was synthesised successfully in high yield.

Expeditious one-pot and solvent-free synthesis of dihydroquinazolin-4(1H)- ones in the presence of microwaves

Dihydroquinazolin-4(1H)-ones were synthesized for the first time by a novel three-component condensation of isatoic anhydride, a primary amine, and an aldehyde catalyzed by Amberlyst-15 in the presence of microwaves under neat conditions. The catalyst is reusable, thus making the process more environmentally friendly. Copyright Taylor & Francis Group, LLC.

One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst

A wide range of mono- and disubstituted dihydroquinazolinones were synthesised via condensation of isatoic anhydride, primary amines, or ammonium salts with aromatic aldehydes in the presence of montmorillonite K-10. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Copyright Taylor & Francis Group, LLC.

Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives

Bisdihydroquinazolinones were synthesized for the first time by a novel pseudo five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent. Georg Thieme Verlag Stuttgart.