1152-07-4

Usage

Uses

Used in Oncology:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as a potential drug candidate for the treatment of cancer due to its anti-tumor effects. It has shown promise in inhibiting tumor growth and progression, making it a valuable compound in the field of oncology.
Used in Epigenetic Research:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as an inhibitor of histone methyltransferase, an enzyme involved in epigenetic regulation. Its potential role in modulating epigenetic processes makes it a valuable tool in the study of gene expression and regulation, with potential applications in the development of targeted therapies for various diseases.
Used in Drug Development:
2-(4-methoxyphenyl)-1H-quinazolin-4-one is used as a lead compound in the development of new drugs, particularly for the treatment of cancer. Its bioactivity and potential therapeutic applications make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 55390-89-1 2-(4-Methoxybenzamido)benzamide 
• 122022-10-0 2,3-dihydro-2-(4-methoxyphenyl)-4(1H)-quinazolinone 
• 28005-57-4 N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 153172-71-5 N-(2-cyanophenyl)-4-methoxybenzamide 
• 85094-63-9 2-(4-methoxyphenyl)-4H-3,1-benzothiazin-4-one 
• 55390-99-3 3-amino-2-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 175794-24-8 4-anthraniloylhydrazono-2,6-di-tert-butyl-2,5-cyclohexadienone 
• 118-48-9 isatoic anhydride 
• 10345-77-4 2-nitro-N,N-diethylbenzamide 
• 874-90-8 4-methoxybenzonitrile 
• 67854-76-6 2-(4-Methoxy-phenyl)-1,2,3,4-tetrahydro-chinazolin 
• 24588-72-5 2-(4-methoxyphenyl)-1,3-dithiane 

Downstream Products

• 55391-00-9 2-(p-methoxyphenyl)-4-chloroquinazoline 
• 1382529-60-3 C₂₂H₁₈N₂OS 
• 1448068-55-0 C₁₆H₁₃N₅O 
• 20800-41-3 2-(4-methoxyphenyl)quinazoline-4(3H)-thione 
• 450401-10-2 C₁₅H₁₄N₄O 
• 1520087-41-5 2-(4-methoxyphenyl)-4-(p-tolyl)quinazoline 
• 1520087-43-7 4-(4-chlorophenyl)-2-(4-methoxyphenyl)quinazoline 
• 84570-80-9 2-(4-methoxylphenyl)-4-phenylquinazoline 
• 71622-66-7 N-(3-methoxyphenyl)-2-(4-methoxyphenyl)quinazolin-4-amine 

Relevant academic research and scientific papers

Metal-free synthesis of quinazolinones without any additives in water

Here we report that an excess amount of aldehyde, in particular, aliphatic aldehyde, without any additives, efficiently facilitates the oxidation of aminal intermediates to quinazolinones in pure water.

An efficient an one-pot method for synthesis of 2-Aryl-(3H)-4-quinazolinones derivatives catalyzed by SSA

A mixture of 2-amino benzamide with aromatic aldehyds in the presence of SSA under solvent-free condition were converted to quinazolinones with good yields.

One pot synthesis of 4(3H)-quinazolinones

Anthranilamides undergo cyclocondensation with aldehydes in presence of iodine in a single-pot reaction to afford 2-substituted 4(3H)-quinazolinones in moderate to excellent yield (40-95%). 2,3-Substituted 4(3H)-quinazolinones are synthesized in moderate to good yield by three-component condensation of isotoic anhydride, amine, and aldehyde in presence of iodine.

N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols

New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.

A bagasse-supported magnetic manganese dioxide nanoparticle: applications in the selective aerobic oxidation of alcohols and one-pot tandem oxidative synthesis of quinazolinones

Magnetic manganese dioxide nanoparticles (MnO2-Fe3O4) were coated on sugarcane bagasse as a sugar industrial waste and bio-support (MnO2-Fe3O4@bagasse) via an in situ reduction strategy, in which potassium permanganate was used as the precursor of MnO2 and sugarcane bagasse as a bio-support and reducing agent of KMnO4. The synthesized bio-based catalyst was characterized by X-ray diffraction, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, Brunauer–Emmett–Teller surface area analysis, and vibrating sample magnetometer analysis. The catalyst was successfully utilized in the selective aerobic oxidation of primary and secondary benzylic alcohols to their corresponding carbonyl compounds and one-pot tandem oxidative synthesis of 2-(substituted)quinazoline-4(3H)-ones from the o-aminobenzamide and aromatic alcohols in the absence of oxidizing reagent or initiator. Graphical abstract: [Figure not available: see fulltext.]

Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.

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.

Electro-oxidative cyclization: Access to quinazolinones: Via K2S2O8without transition metal catalyst and base

A K2S2O8-promoted oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones was successfully achieved under undivided electrolytic conditions without a transition metal and base. The key feature of this protocol is the utilization of K2S2O8 as an inexpensive and easy-to-handle radical surrogate that can effectively promote the reaction via a simple procedure, leading to the formation of nitrogen heterocycles via direct oxidative cyclization at room temperature in a one-pot procedure under constant current. Owing to the use of continuous-flow electrochemical setups, this green, mild and practical electrosynthesis features high efficiency and excellent functional group tolerance and is easy to scale up.

Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution

The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.

Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide

A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.