Novel environmentally benign procedure for the synthesis of 2‐aryl‐ and 2‐hetaryl‐4(3<i>H</i>)‐quinazolinones

Deligeorgiev, Todor; Kaloyanova, St.; Vasilev, Aleksey; Vaquero, J. J.; Alvárez‐Builla, Julio; Cuadro, Ana M.

doi:10.1111/j.1478-4408.2010.00223.x

Cited by 15 publications

(5 citation statements)

References 20 publications

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“…Direct synthesis of carboxylic acids and their derivatives via palladium-catalyzed carbonylation of aryl halides and C–H bonds followed by intramolecular or intermolecular carboxamidation indeed represents a direct and convenient synthetic strategy for quinazolin-4(3 H )-ones. Other synthetic routes include condensation of o -aminobenzamide with aryl methyl ketones and keto alkynes …”

Section: Introductionmentioning

confidence: 99%

One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols

et al. 2017

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In this paper, we report a general, efficient, and environmentally benign method for the one-pot cascade synthesis of quinazolin-4(3H)-ones via acceptorless dehydrogenative coupling of o-aminobenzamide with alcohols catalyzed by a simple Ni(II) catalyst, [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinazolin-4(3H)-ones were synthesized in high yields starting from readily available benzyl alcohols and o-aminobenzamides. Several controlled reactions along with deuterium labeling studies were carried out to establish the acceptorless dehydrogenative nature of the reactions.

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Section: Introductionmentioning

confidence: 99%

One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols

et al. 2017

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“…Phenylacetylenes substituted with electron-withdrawing groups (EWGs) such as F, Br, CF 3 , CN, and NO 2 also produced the corresponding quinazolin-4(3 H )-ones in good yields (e.g., 2g–k ). Further, the acetylenes with fused bicyclics and biphenyl rings (e.g., 2m and 2n ) and heterocycles (e.g., 2o ) also participated well in this reaction; however in the case of 9-ethynylanthracene, the desired product was obtained only in traces (e.g., 2p ) . Unfortunately, aliphatic alkynes were not suitable for this kind of transformations under our optimized conditions.…”

Section: Results and Discussionmentioning

confidence: 93%

Discovery of Quinazolin-4(3H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation

et al. 2019

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NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C−C triple/ double bond and the release of formaldehyde. The reaction relies on the C−N bond formation along with the C−C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC 50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.

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“…[ 54 ] Besides, another strategy for preparing quinazolinone was achieved from anthranilamide XVIII via condensation with different aromatic aldehydes in the presence of PTSA in polyethylene glycol (PEG‐200/400) as a green solvent under microwave irradiations for 5–10 min (Pathway R). [ 55 ] Also, reacting anthranilamide XVIII with potassium isopropyldithiocarbonate in DMF under solvent‐free conditions afforded 2‐mercaptoquinazolinone derivative (Pathway S). [ 56 ] Furthermore, 2,3‐disubstituted‐4(3 H )‐quinazolinones were synthesized through a three‐component reaction between isatoic anhydride ( XIX) , amines and, ortho‐esters (Pathway T).…”

Section: Synthetic Routes Of Quinazoline Derivativesmentioning

confidence: 99%

A literature review on pharmacological aspects, docking studies, and synthetic approaches of quinazoline and quinazolinone derivatives

Ghoneim,

Abdelgawad,

Elkanzi

et al. 2024

Archiv der Pharmazie

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Quinazoline and quinazolinone derivatives piqued medicinal chemistry interest in developing novel drug candidates owing to their pharmacological potential. They are important chemicals for the synthesis of a variety of physiologically significant and pharmacologically useful molecules. Quinazoline and quinazolinone derivatives have anticancer, anti‐inflammatory, antidiabetic, anticonvulsant, antiviral, and antimicrobial potential. The increased understanding of quinazoline and quinazolinone derivatives in biological activities provides opportunities for new medicinal products. The present review focuses on novel advances in the synthesis of these important scaffolds and other medicinal aspects involving drug design, structure–activity relationship, and action mechanisms of quinazoline and quinazolinone derivatives to help in the development of new quinazoline and quinazolinone derivatives.

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Novel environmentally benign procedure for the synthesis of 2‐aryl‐ and 2‐hetaryl‐4(3H)‐quinazolinones

Cited by 15 publications

References 20 publications

One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols

One-Pot Cascade Synthesis of Quinazolin-4(3H)-ones via Nickel-Catalyzed Dehydrogenative Coupling of o-Aminobenzamides with Alcohols

Discovery of Quinazolin-4(3H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation

A literature review on pharmacological aspects, docking studies, and synthetic approaches of quinazoline and quinazolinone derivatives

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