353467-22-8

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 118-48-9 isatoic anhydride 

Downstream Products

• 138867-16-0 2-(2-fluorophenyl)quinazolin-4(3Η)-one 
• 610276-36-3 C₁₄H₉FN₂S 
• 610276-35-2 C₁₄H₁₁FN₄ 
• 1448068-39-0 C₁₅H₁₀FN₅ 

Relevant academic research and scientific papers

Microwave-accelerated three components cyclocondensation in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones promoted by Cu-CNTs

Cu-CNTs efficiently catalyzes condensation reaction of isatoic anhydride, aldehydes, and primary amines or ammonium acetate to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives successfully in high yield. The protocol proves to be effic

KOH/DMSO: A basic suspension for transition metal-free Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones

A novel protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-aminobenzamides and aldehyde derivatives catalyzed by KOH/DMSO suspension has been developed. The present transition metal free methodology is operationally simple, scalable and varieties of 2,3-dihydroquinazolin-4(1H)-one derivatives were obtained in good to excellent yields in short reaction times.

Boosting Enantioselectivity of Chiral Organocatalysts with Ultrathin Two-Dimensional Metal-Organic Framework Nanosheets

The development of methodologies for inducing and tailoring enantioselectivities of catalysts is an important issue in asymmetric catalysis. In this work, we demonstrate for the first time that chiral molecular catalysts can be boosted from completely nonselective to highly enantioselective when installed in nanostructured metal-organic frameworks (MOFs). Exfoliation of layered crystals is one of the most direct synthetic routes to unltrathin nanosheets, but its use in MOFs is limited by the availability of layered MOFs. We illustrate that layered MOFs can be designed using ligand-capped metal clusters and angular organic linkers. This leads to the synthesis of two three-dimensional (3D) layered porous MOFs from Zn4-p-tert-butylsulfonyl calix[4]arene and chiral angular 1,1′-binaphthol/-biphenol dicarboxylic acids, which can be ultrasonic exfoliated into one- and two-layer nanosheets. The obtained MOF materials are efficient catalysts for asymmetric cascade condensation and cyclization of 2-aminobenzamide and aldehydes to produce 2,3-dihyroquinazolinones. While both binaphthol and biphenol display no enantioselectivity, restriction of their freedom in the MOFs leads to 56-90% and 46-72% ee, respectively, which are increased to 72-94% and 64-82% ee after exposure to external surfaces of the flexible nanosheets. Moreover, the MOF crystals and nanosheets exhibit highly sensitive fluorescent enhancement in the presence of chiral amino alcohols with enantioselectivity factors being, respectively, increased up to 1.4 and 2.3 times of the values of the diols, allowing them to be utilized in chiral sensing. Therefore, the observed enantioselectivities increase in the order organocatalyst MOF crystals MOF nanosheets in both catalysis and sensing. This work not only provides a strategy to make 3D layered MOFs and their untrathin nanosheets but also paves the way to utilize nanostructured MOFs to manipulate enantioselectivities of molecular catalysts.

Sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives

The invention discloses a sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives. The dihydro-quinazolinone and quinazolinone derivatives are controllably prepared through a cascade reaction of anthranilamide or derivatives thereof and an aldehyde compound by taking sulfonic acid ionic liquid as a catalyst. Under the set catalytic reaction condition, the conversion rate of raw materials reaches up to 99%, and the yield of dihydro-quinazolinone and the yield of quinazolinone both can reach 95%. Compared with the prior art, the green solvent-ionic liquid is taken as the catalyst, no additional oxidizing agent or heavy metal catalyst is needed, the advantages that the reaction conditions are mild, environmental friendliness is achieved, the reaction selectivity and the product yield are high, controllable synthesis is achieved, and the catalyst can be recycled and reused conveniently are achieved, and the novel method is friendly to environment and efficient in synthesis.

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.

Method for synthesis of quinazolinone derivative

The invention discloses a method for synthesis of quinazolinone; the method comprises the steps of starting from o-aminobenzamide, taking water as a solvent, carrying out a ring-enlargement reaction with benzaldehyde, to generate a dihydroquinazolinone intermediate, and then under participation of a metal iridium complex, dehydrogenating to obtain the quinazolinone derivative; the reaction shows three remarkable advantages: 1) the reaction is carried out in an aqueous solution so as to reduce use of a large amount of organic solvents, and water is a cheap, green and safe solvent; 2) the reaction avoids use of highly toxic oxidants, so as to avoid damage to the environment; and 3) hydrogen gas generated from the reaction is a by-product, and has no environmental pollution; therefore, the reaction accords with the requirements of green chemistry, and has broad prospects for development.

One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst

Abstract: A series of 2,3-dihydroquinazolin-4(1H)-ones have been synthesized with good to excellent yields by one-pot reaction using isatoic anhydride, aldehydes, and ammonium acetate or amines in acetonitrile in the presence of 4 ? molecular sieve modified with lanthanum(III) as an efficient heterogeneous catalyst. The catalyst could be reused without evident loss of activity. Graphical Abstract: [Figure not available: see fulltext.]

Discovery of potent and selective nonplanar tankyrase inhibiting nicotinamide mimics

Diphtheria toxin-like ADP-ribosyltransferases catalyse a posttranslational modification, ADP-ribosylation and form a protein family of 17 members in humans. Two of the family members, tankyrases 1 and 2, are involved in several cellular processes including mitosis and Wnt/β-catenin signalling pathway. They are often over-expressed in cancer cells and have been linked with the survival of cancer cells making them potential therapeutic targets. In this study, we identified nine tankyrase inhibitors through virtual and in vitro screening. Crystal structures of tankyrase 2 with the compounds showed that they bind to the nicotinamide binding site of the catalytic domain. Based on the co-crystal structures we designed and synthesized a series of tetrahydroquinazolin-4-one and pyridopyrimidin-4-one analogs and were subsequently able to improve the potency of a hit compound almost 100-fold (from 11 μM to 150 nM). The most potent compounds were selective towards tankyrases over a panel of other human ARTD enzymes. They also inhibited Wnt/β-catenin pathway in a cell-based reporter assay demonstrating the potential usefulness of the identified new scaffolds for further development.

Application of the ultrasound in the mild synthesis of substituted 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heterogeneous metal-MWCNTs nanocomposites

A practical method were applied successfully to synthesize mono- and disubstituted dihydroquinazolinones through three-component condensation of isatoic anhydride, primary amines or ammonium acetate with aromatic aldehydes in the presence of some transiti

Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO3H as a recyclable catalyst

A new β-cyclodextrin-SO3H-assisted, convenient and efficient strategy for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media is described. The catalyst can be readily recovered and reused for the next reaction for at least three runs without any significant impact on the yields of the products. The main advantages of this protocol include short reaction times, practical simplicity, high yields, recyclable catalysts, safety, and cheapness of benign solvents. This journal is the Partner Organisations 2014.