77726-78-4

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIMETHYL-1,2,3-TRIHYDROQUINAZOLIN-4-ONE is used as a building block for the synthesis of various pharmaceuticals due to its versatile reactivity and potential therapeutic properties. Its potential antiviral and anticancer properties make it a promising candidate for the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2-DIMETHYL-1,2,3-TRIHYDROQUINAZOLIN-4-ONE is utilized as a key component in the synthesis of agrochemicals, contributing to the development of effective pest control agents and other agricultural products.
Used in Dye and Pigment Production:
2,2-DIMETHYL-1,2,3-TRIHYDROQUINAZOLIN-4-ONE is used as an intermediate in the production of dyes and pigments, leveraging its chemical properties to create a range of colorants for various applications.
Used in Organic Chemistry Research:
DTQ's unique structure and reactivity make it a valuable compound for research in organic chemistry, where it can be employed to explore new reactions, mechanisms, and the synthesis of novel organic compounds.

Upstream product

• 28144-70-9 anthranilic acid amide 
• 67-64-1 acetone 
• 67-63-0 isopropyl alcohol 
• 542-08-5 isopropyl acetoacetate 
• 141-97-9 ethyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 108-18-9 diisopropylamine 
• 3424-21-3 triisopropylamine 
• 1885-29-6 anthranilic acid nitrile 

Downstream Products

• 1769-24-0 2-methyl-4-quinazolone 

Relevant academic research and scientific papers

Real time HR-MAS NMR: Application in reaction optimization, mechanism elucidation and kinetic analysis for heterogeneous reagent catalyzed small molecule chemistry

A novel application of in situ 1H high-resolution magic angle spinning (HR-MAS) NMR technique for real-time monitoring of H2SO 4-silica promoted formation of 2, 2-disubstituted quinozolin-4(3H)-ones is reported. The detailed NMR spectroscopic data led to elucidation of the mechanism, reaction optimization, kinetics and quantitative analysis of the product accurately and efficiently. The translation of the optimized parameters obtained by 1H HR-MAS NMR in the wet laboratory provided similar results. It is proposed that 1H HR-MAS has a potential utility for optimization of various organic transformations in solid supported catalyzed reactions. Copyright

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.

Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives

A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.

Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation

Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.

Selective synthesis of functionalized quinazolinone derivatives via biocatalysis

A novel and efficient biocatalyzed methodology for the construction of functionalized quinazolinone derivatives via tandem / hydrolysis / decarboxylation / cyclization and transesterification reactions has been developed that works with a variety of 2-aminobenzamide and β-dicarbonyl compounds. This method requires mild conditions, and has demonstrated high catalytic activity, excellent yields, excellent chemoselectivity, and a broad substrate scope. Additionally, biocatalyzed decarboxylation does not require high temperatures or light activation, giving it a substantial advantage over alternative techniques. Most importantly, it offers a new example for the exploration of simple, convenient, and environmentally friendly synthetic routes utilizing enzymes in organic chemistry.

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.

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 Remarkable Cooperative Effect of a Br?nsted-Acidic Ionic Liquid in the Cyclization of 2-Aminobenzamides with Ketones

An unprecedented role of an imidazolium Br?nsted acidic ionic liquid was found in the formation of 2,2-disubstituted quinazolin-4(1H)-one derivatives; both the C2-H of the imidazolium moiety and an acidic proton were necessary and simultaneously took part in the catalysis. A library of quinazolin-4(1H)-ones was prepared from readily available ketones and 2-aminobenzamides; excellent yields were obtained through simple crystallization under solvent-free conditions with lower E factors. The catalyst could be reused over five consecutive runs without any significant loss in catalytic activity. This method produces only water as a byproduct and represents a green synthetic protocol. A clean reaction, no chromatographic purification, easily accessible reactants, a metal-free and solvent-free process, and environmentally friendly reaction conditions are the notable advantages of this procedure. The possible role of the C2-H of the imidazolium moiety in catalysis was studied by mass spectrometry.

Facile method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by SiO2–H3PW12O40 in water

The 12-tungstophosphoric acid supported on silica gel (PW/SiO2) exhibits excellent activity in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with carbonyl compounds in water under reflux conditions. The desired products have been obtained in short reaction times in high yields. Our method has been successfully applied for both aldehydes and ketones (aromatic and aliphatic). Easy recovery and reusable catalyst, easy work-up and avoidance of using harmful organic solvents are the major advantages of our method in comparison to existing methods.

Expeditious synthesis of 2,3-dihydroquinazolin-4(1H)-ones in aqueous medium using thiamine hydrochloride (VB1) as a mild, efficient, and reusable organocatalyst

A simple and straightforward synthesis of 2,3-dihydroquinazolin-4(1H)-ones is developed by reacting anthranilamide with various aldehydes or ketones under mild reaction conditions, using thiamine hydrochloride as a cost-effective, readily available, and green catalyst in water. Simple purification process, high yields within short reaction time, wide substrate scope, operational simplicity, and reusability of the catalyst up to three cycles enrich the applicability of the protocol.