107922-06-5

Basic information

• Product Name: 2-(3, 4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• Synonyms: 2-(3, 4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one
• CAS NO: 107922-06-5
• Molecular Weight: 240.261
• Mol File: 107922-06-5.mol

Chemical Properties

• CAS DataBase Reference: 2-(3, 4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3, 4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one(107922-06-5)
• EPA Substance Registry System: 2-(3, 4-dihydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one(107922-06-5)

Safety Data

• Hazardous Substances Data: 107922-06-5(Hazardous Substances Data)

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 118-48-9 isatoic anhydride 

Relevant articles and documents

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by α-chymotrypsin

We discovered that α-chymotrypsin has a promiscuous ability to catalyze the cyclocondensation of aromatic and aliphatic aldehydes with 2-aminobenzamides to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones successfully in high yields (90%–98%) under alcohol solvent. The catalytic activity of α-chymotrypsin was evaluated through investigating the temperature, the enzyme loading and the ratio of substrates in the enzyme-catalyzed reactions. The present method proves to be efficient and environmentally friendly in terms of short reaction time, high yield, green catalyst and the clean products obtained without further purification processes.

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.

Larvicidal activities of 2-aryl-2,3-dihydroquinazolin -4-ones against malaria vector anopheles arabiensis, in silico ADMET prediction and molecular target investigation

Malaria, affecting all continents, remains one of the life-threatening diseases introduced by parasites that are transmitted to humans through the bites of infected Anopheles mosquitoes. Although insecticides are currently used to reduce malaria transmission, their safety concern for living systems, as well as the environment, is a growing problem. Therefore, the discovery of novel, less toxic, and environmentally safe molecules to effectively combat the control of these vectors is in high demand. In order to identify new potential larvicidal agents, a series of 2-aryl-1,2-dihydroquinazolin-4-one derivatives were synthesized and evaluated for their larvicidal activity against Anopheles arabiensis. The in silico absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of the compounds were also investigated and most of the derivatives possessed a favorable ADMET profile. Computational modeling studies of the title compounds demonstrated a favorable binding interaction against the acetylcholinesterase enzyme molecular target. Thus, 2-aryl-1,2-dihydroquinazolin-4-ones were identified as a novel class of Anopheles arabiensis insecticides which can be used as lead molecules for the further development of more potent and safer larvicidal agents for treating malaria.

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.

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.].

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.

Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3

2,3-Dihydroquinazolin-4(1H)-one derivatives have been synthesized via one-pot reaction of isatoic anhydride, aromatic aldehyde, and ammonium acetate catalyzed by FeCl3/neutral Al2O3 in tert-butanol under reflux conditions.

Sulfuric acid heterogenized on magnetic Fe3O4 nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions

Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs-OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco-friendly advantages of this catalytic system. It is noteworthy that this catalytic system is applicable to a wide range of spectrum of aromatic aldehydes, and the desired products were obtained in good to excellent yields under mild conditions. The use of ecofriendly solvents makes also this synthetic protocol ideal and fascinating from the environmental point of view.

Sulfamic acid immobilized on amino-functionalized magnetic nanoparticles: A new and active magnetically recoverable catalyst for the synthesis of N-heterocyclic compounds

Sulfamic acid immobilized on amino-functionalized magnetic nanoparticles (MNPs/DETA-SA) was successfully fabricated and characterized using various techniques. Diameters of approximately 15?nm for the MNPs/DETA-SA were observed from scanning electron microscopy images. The as-fabricated nanocomposite was applied as an efficient and magnetically reusable catalyst for the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives. All products were obtained in good to excellent yields. Recovery tests confirm that the catalyst can be readily recovered using an external magnet and reused many times without significant loss of its catalytic activity.

Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two novel nanostructured catalysts: applications in the synthesis of Biginelli-type, polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives

Abstract: Nanometasilica disulfuric acid (NMSDSA) and nanometasilica monosulfuric acid sodium salt (NMSMSA) as two nanostructured novel, green and heterogeneous catalysts were designed, synthesized and fully characterized by FT-IR, energy-dispersive X-ray spectroscopy, X-ray diffraction patterns, scanning electron microscopy, transmission electron microscopy and thermal gravimetric analysis. Then their catalytic applications were studied in the Biginelli-type reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via one-pot three-component condensation reaction between several aldehydes, ethyl acetoacetate and urea or thiourea. To further study catalytic properties of NMSDSA and NMSMSA, they were used in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives under same reaction conditions. NMSDSA and NMSMSA have advantages such as cost-effectiveness, cleaner reaction profile, benign and heterogeneous characters, reusability of the catalysts and being in agreement with the green chemistry protocols. The described nanostructured catalysts have natural-based acids and potential for industrial production. Graphical Abstract: Synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives via Biginelli-type reaction, polyhydroquinolines and 2,3-dihydroquinazolin-4(1H)-ones using NMSDSA and NMSMSA as two novel nanostructured catalysts. [Figure not available: see fulltext.]