1788-95-0

Usage

Structure

Contains a bromophenyl group

Use

Often used in pharmaceutical research and drug development

Potential therapeutic properties

Promising candidate for the development of new drugs

Other applications

Unique chemical structure may also make it useful in organic chemistry

InChI:InChI=1/C15H11BrN2O/c1-10-17-14-5-3-2-4-13(14)15(19)18(10)12-8-6-11(16)7-9-12/h2-9H,1H3

Upstream product

• 106-40-1 4-bromo-aniline 
• 89-52-1 o-acetylamino-benzoic acid 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 615-43-0 2-iodophenylamine 
• 108-24-7 acetic anhydride 
• 586-78-7 para-nitrophenyl bromide 
• 118-92-3 anthranilic acid 
• 50735-55-2 2-amino-N-(4-bromophenyl)benzamide 
• 24122-32-5 3-(4-bromophenyl)-4(3H)-quinazolinone 
• 84770-68-3 2-Methyl-3-(4'-bromophenyl)-1,2,3,4-tetrahydroquinazolin-4-one 
• 118-48-9 isatoic anhydride 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 73283-33-7 2-[2-Oxo-2-(2-pyridyl)ethyl]-3-p-bromophenyl-4(3H)-quinazolinone 
• 73283-34-8 2-[2-Oxo-2-(3-pyridyl)ethyl]-3-p-bromophenyl-4(3H)-quinazolinone 
• 73283-35-9 2-[2-Oxo-2-(4-pyridyl)ethyl]-3-p-bromophenyl-4(3H)-quinazolinone 
• 128457-99-8 3-(4-Bromo-phenyl)-2-((E)-3-oxo-3-p-tolyl-propenyl)-3H-quinazolin-4-one 
• 128457-95-4 3-(4-Bromo-phenyl)-2-((E)-3-oxo-3-phenyl-propenyl)-3H-quinazolin-4-one 
• 131532-68-8 3-(4-Bromo-phenyl)-4-oxo-3,4-dihydro-quinazoline-2-carbaldehyde 
• 84770-68-3 2-Methyl-3-(4'-bromophenyl)-1,2,3,4-tetrahydroquinazolin-4-one 
• 73283-32-6 2-(3,3,3-Trifluoroacetonyl)-3-p-bromophenyl-4(3H)-quinazolinone 
• 388617-89-8 (E)-3-(4-bromophenyl)-2-(4-fluorostyryl)quinazolin-4(3H)-one 
• 131532-96-2 3-(4-Bromo-phenyl)-2-{[4-phenyl-3-p-tolyl-3H-thiazol-(2Z)-ylidene]-hydrazonomethyl}-3H-quinazolin-4-one 
• 128458-17-3 3-(4-Bromo-phenyl)-2-[2-(4-bromo-phenyl)-5-p-tolyl-2H-pyrazol-3-yl]-3H-quinazolin-4-one 
• 128458-09-3 3-(4-Bromo-phenyl)-2-(2,5-di-p-tolyl-2H-pyrazol-3-yl)-3H-quinazolin-4-one 
• 131533-06-7 3-(4-Bromo-phenyl)-2-{[4-oxo-3-p-tolyl-thiazolidin-(2Z)-ylidene]-hydrazonomethyl}-3H-quinazolin-4-one 
• 128458-13-9 3-(4-Bromo-phenyl)-2-[2-(4-bromo-phenyl)-5-phenyl-2H-pyrazol-3-yl]-3H-quinazolin-4-one 

Relevant academic research and scientific papers

A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3H)-one derivatives in Green media

The novel organic-inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS-guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivativesviathree-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a-q). XRD, FT-IR, FE-SEM, TGA, VSM and EDX were used to characterize this new magnetic organocatalyst. Outstanding performance, short response time (15-30 min), simple operation, easy work-up procedure, and avoidance of toxic catalysts can be regarded as its significant advantages. Moreover, it can be easily separated from the reaction solution through magnetic decantation using an external magnet, and recycled at least six times without notable reduction in its activity.

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.

Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol

In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.

Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation

A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.

Expeditious synthesis and spectroscopic characterization of 2-methyl-3-substituted-quinazolin-4(3H)-one derivatives

Quinazoline and quinazolinone derivatives are well-known bioactive heterocycles owing to their therapeutic diversity and extensive medicinal application in drug design and pharmaceutics. A series of 2-methyl-3-substituted quinazolin-4(3H)-one derivatives 8a-q was herein synthesized from synthetic conversion of anthranilic acid to 2-methyl-4H-3,1-benzoxazi-4-one, 7 which was subsequently transformed to the targeted 2,3-disubstituted quinazolin-4(3H)-one derivatives 8a-q by reacting with some notable amino-containing moieties via an ameliorable pathway. The catalyst-free synthesis was successful achieved by careful reaction optimization study using solvent choice and reaction temperature variability as key parameters. The chemical structures of the synthesized compounds were confirmed by IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data.

Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.

Synthesis, biological evaluation and structure-activity relationship of 2-styrylquinazolones as anti-tubercular agents

2-Styrylquinazolones are reported as a novel class of potent anti-mycobacterial agents. Forty-six target compounds have been synthesized using one pot reaction involving isatoic anhydride, amine, and triethyl orthoacetate followed by aldehyde to construct

Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs

Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.

An efficient one-pot access to quinazolinone derivatives using TiO 2 nanoparticles as catalyst: Synthesis and vasorelaxant activity evaluation

A variety of quinazolinone derivatives were successfully synthesized, via a three-component condensation reaction between anthranilic acid, acetic anhydride, and amines. This process was accomplished in the presence of catalytic amount of titanium dioxide

Studies on arylfuran derivatives - Part IV. Synthesis and antibacterial properties of arylfurylvinylquinazolinones

A number of arylfurylvinylquinazolinones were prepared as possible antibacterial agents. The structural elucidations of all the compounds were carried out on the basis of analytical and spectral data. The newly synthesized compounds were screened for their antibacterial properties against both Gram-positive and Gram-negative bacteria.