74375-30-7

Upstream product

• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 75-04-7 ethylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 74375-38-5 3-ethyl-2-phenylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

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.

Metal-Free Oxidative C(sp 3)-N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones

A metal-free oxidative C(sp 3)-N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1 H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1 H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.

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.]

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.

Inclusion complex of Isatoic anhydride with β-cyclodextrin and supramolecular one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous media

The inclusion complex of isatoic anhydride with β-cyclodextrin was formed as a result of intermolecular interaction between isatoic anhydride with β-CD. The inclusion complex was confirmed by IR spectroscopy, X-ray diffraction and DSC studies. From application of complex, herein we have described a simple and efficient protocol for synthesis of 2, 3-dihydroquinazoline-4(1H)-one derivatives by one pot condensation of isatoic anhydride, ammonium acetate or amine and aldehyde using β-CD as a supramolecular catalyst in aqueous media.

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.

Cation-exchange resin as an efficient hetero- Geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones

Various mono- and disubstituted 2,3-dihydro-4(1H)-quinazolinones were synthesized efficiently by a one-pot three-component condensation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines using a strong acidic cation-exchange resin as the catalyst in EtOH-H2O solution. The catalyst is cheap, efficient, stable, and reusable under the reaction conditions. The novel method offers several advantages, such as excellent yields, environmentally friendly reaction media, and simple procedure.

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.

Strontium chloride-catalyzed one-pot synthesis of 2, 3-dihydroquinazolin- 4(1H)-ones in protic media

A wide range of mono- and disubstituted 2, 3-dihydroquinazolin-4(1H)-ones were obtained in high yields by condensation of isatoic anhydride, aldehydes with ammonium salts or primary amines in the presence of strontium chloride in aqueous ethanol under reflux.

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.