386242-54-2

Upstream product

• 28144-70-9 anthranilic acid amide 
• 456-48-4 3-Fluorobenzaldehyde 
• 456-41-7 1-(Bromomethyl)-3-fluorobenzene 
• 1885-29-6 anthranilic acid nitrile 
• 612-24-8 o-nitrobenzonitrile 
• 118-48-9 isatoic anhydride 

Downstream Products

• 138867-17-1 2-(meta-fluoro)phenylquinazolin-4(3H)-one 
• 1448068-40-3 C₁₅H₁₀FN₅ 
• 1275568-98-3 C₁₄H₁₁FN₄ 
• 1448068-89-0 2-(3-fluorophenyl)-3H-quinazoline-4-thione 

Relevant academic research and scientific papers

Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of nanocomposites under microwave irradiation

The preparation of quinazolinones has been developed by the condensation of aromatic aldehydes and 2-aminobenzamide in the presence of transition metal-CNTs nanocomposites as novel and recyclable catalyst under microwave and solvent-free conditions. This methodology provides a high speed path for the green and mild synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones with high structural diversity. The present methodology has advantages such as high activity and reusability of catalysts, heterogeneous nature of catalysts, no use of hazardous organic solvents and green conditions.

Copper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol-Water

A copper-catalyzed one-pot synthesis of 2,3-dihydroquinazolin-4(1 H)-ones with diboronic acid as a reductant in an aqueous medium is described. Various 2,3-dihydroquinazolin-4(1 H)-ones were prepared with good functional-group tolerance in good yields under mild conditions from readily available 2-nitrobenzonitriles and various carbonyl compounds.

Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature

A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.

Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

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.

Green protocol for synthesis of 2,3-dihydroquinazolin-4(1H)-ones: lactic acid as catalyst under solvent-free condition

Abstract: In the present work, lactic acid was used as novel, green catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via two distinct methods, including reaction of 2-aminobenzamide with aldehydes/ketones or isatoic anhydride with ammonium acetate and aldehydes in neat condition at 70?°C. The desired products were obtained in satisfactory yields. Short reaction time, easy workup, and more importantly environmental benignity are the most outstanding advantages of these procedures. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by succinimide-N-sulfonic acid as a mild and efficient catalyst

A simple, green and environmentally benign procedure was developed for the synthesis of 2,3-dihydro-2-phenylquinazolin-4(1H)-ones using catalytic amounts of succinimide-N-sulfonic acid via the cyclocondensation of 2-aminobenzamide with an aldehyde. The present methodology offers several advantages such as high yields, simple procedure, low cost, short reaction times, mild reaction conditions, and use of a reusable catalyst.

Supported ceric ammonium nitrate: A highly efficient catalytic system for the synthesis of diversified 2,3-substituted 2,3-dihydroquinazolin-4(1 H)-ones

A practically expeditious protocol has been developed for the cascade synthesis of 2,3 dihydroquinazolin-4(1H)-ones via the condensation of 2-aminobenzamide/2-aminoben-zanilide and aromatic aldehydes using a catalytic amount of silica-supported ceric ammonium nitrate. This method affords rapid transformation at room temperature with good to excellent yields.

Environmentally friendly synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)- ones by novel Co-CNTs as recoverable catalysts

The objective of this study is to investigate the possibility of using Co-CNTs as a green reaction medium and a catalyst for the cyclo-condensation of o-aminobenzamide with various aldehydes. This inexpensive, non-toxic, and readily available catalyst efficiently catalyzes the above condensation for the synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones. Compared to the classical reaction, this is a simple, highly yielding, time saving, and environmentally friendly method.