108367-37-9

Upstream product

• 28144-70-9 anthranilic acid amide 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 118-48-9 isatoic anhydride 
• 631-61-8 ammonium acetate 
• 101280-42-6 N-(2,4-dimethoxy-benzyliden)-anthranilic acid amide 

Downstream Products

• 132982-02-6 2-(2,4-dimethoxyphenyl)quinazolin-4(3H)-one 

Relevant academic research and scientific papers

Sulfamic acid as a reusable and green catalyst for efficient and simple synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in water or methanol

A series of 2,3-dihydroquinazolin-4(1H)-ones have been synthesized in good to excellent yields through direct cyclocondensation of anthranilamide and aryl aldehydes or ketones in water or methanol under mild conditions. The reaction was efficiently promoted by 10 mol% sulfamic acid (SA, H2NSO 3H) and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity.

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by nano-Fe3O4/TiCl2/cellulose as a bio-based magnetic catalyst

Abstract: Nano-Fe3O4/TiCl2/cellulose as a new, green, bio-based and recyclable catalyst was synthesized by bonding TiCl4 to hydroxyl groups of nano-cellulose and Fe3O4 nanoparticles. This catalyst was characterized by FT-IR, FESEM, TEM, XRF, BET, VSM, EDX and XRD. As a first report, the catalytic activity of nano-Fe3O4/TiCl2/cellulose was investigated in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in good to excellent yields under mild conditions. Graphical abstract: [Figure not available: see fulltext.]

Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media

An efficient and straightforward approach to the synthesis of 2,3-dihydroquinazolin-4(1H)-one from 2-aminobenzamide and carbonyl compounds (aldehydes and ketones) using biocompatible choline sulfate-based acidic ionic liquid as a cheap and readily available catalyst in water has been developed. Various 2,3-dihydroquinazolin-4(1H)-one have been prepared using low-cost and environmental friendly solvent and catalyst in good to excellent yields in a shorter reaction time. The choline sulfate catalyst was prepared using a simple method from readily available starting material and was confirmed by 1H NMR, FTIR, and TGA. The ease of the product separation without organic solvent and column chromatography and the reusability of the acidic ionic liquid catalyst makes this method economically affordable for large-scale synthesis.

Poly(4-vinylpyridine) supported acidic ionic liquid: A novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation

A novel poly(4-vinylpyridine) supported acidic ionic liquid catalyst was synthesized by the reaction of 4-vinylpyridine with 1,3-propanesultone, followed by the polymerization and the addition of the heteropolyacid. Due to the combination of polymer features and ionic liquid, it acted as a heterogeneous catalyst to effectively catalyze the cyclocondensation reaction of anthranilamide with aldehydes under ultrasonic irradiation and afforded the corresponding 2,3-dihydro-4(1H)-quinazolinones compounds in good to excellent yields. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity. More importantly, the use of ultrasonic irradiation can obviously accelerate the reaction.

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence of Fe3O4@nano-cellulose–OPO3H as a bio-based magnetic nanocatalyst

In this research, we have used Fe3O4@nano-cellulose–OPO3H as magnetic bio-based nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via condensation of 2-aminobenzamide and different aldehydes. The major advantages of the present methodology are good yields, ecofriendly catalyst, and easy workup.

Facile and efficient protocols for C–C and C–N bond formation reactions using a superparamagnetic palladium complex as reusable catalyst

Abstract: Facile and efficient protocols for some multicomponent coupling reactions such as the Suzuki reaction and synthesis of polyhydroquinoline and 2,3-dihydroquinazoline-4-(1H)-one derivatives using a superparamagnetic palladium complex as catalyst have been developed. Graphical abstract: [Figure not available: see fulltext.].

SbCl3 as effective catalyst for the preparation of 2,3-Dihydroquinazolin-4(1H)-ones, spectroscopic investigation and DFT study

A simple and efficient method has been developed for the synthesis of Quinazolines using SbCl3 as a heterogeneous catalysis at room temperature. This method provides a good pathway for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones derivatives in the terms of excellent yields and short reaction times. Also we studied theoretically and experimentally on 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (PDQ). Using density functional theory (DFT), the tautomerism of PDQ was also studied. Thermal stability of PDQ was studied by thermo gravimetric analysis (TGA). The spectroscopic results and theoretical calculations indicate that the strength of intramolecular hydrogen bonding (IHB) of PDQ is stronger than that in 2-methyl-4-quinolinol (2MQ). The absorption spectra of the PDQ in solvents with different polarity were obtained and the results show that PDQ exists in both keto-amine and enol-imine forms in THF, while it has keto-amine form in other solvents. Theoretical results show that the conductance of the two tautomers (keto-amine and enol-imine) varies greatly, which offers that the potential usage of this molecule is as a molecular device.

Synthesis and characterization of bromine source supported on magnetic Fe3O4 nanoparticles: A new, versatile and efficient magnetically separable catalyst for organic synthesis

Tribenzylammonium tribromide supported onto magnetic nanoparticles (Br3-TBA-Fe3O4) as a bromine source was successfully synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy and vibrating sample magnetometry. The synthesized catalyst is shown to be a versatile and highly efficient heterogeneous catalyst for the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-one and polyhydroquinoline derivatives. To the best of the authors' knowledge, this is the first report of the use of a bromine source immobilized on Fe3O4 nanoparticles as a magnetically separable catalyst for these reactions. The nanosolid catalyst can be magnetically recovered and reused readily several times without significant loss in catalytic efficiency.

Potential anti-proliferative agents from 1,4-benzoxazinone-quinazolin-4(3H)-one templates

A novel synthetic protocol has been developed for the synthesis of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids 7a–n by employing Pd-catalyzed C[sbnd]H arylation in presence of 5–10% phosphine ligand in good to excellent yields and evaluated for their anti-proliferative activity against three cancer cell lines such as A549 (lung), HeLa (cervical), MDA-MB-231 (breast). Compounds 7d, 7f, 7l and 7n exhibited promising anti-proliferative activity with GI50 values ranging from 0.37 to 2.73 μM respectively against A549, HeLa, and MDA-MB-231, while compound 7f showed significant activity against MDA-MB-231 with GI50 value 0.58 μM, 7j showed significant activity against A549 with GI50 value 0.32 μM and 7l showed significant activity against HeLa with GI50 value 0.37 μM. This is the first report on the synthesis and in vitro anti-proliferative evaluation of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids.

Application of SBA-Pr-SO3H in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones: characterization, UV–Vis investigations and DFT studies

An efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives 4a–l is described using SBA-Pr-SO3H as a heterogeneous acid catalyst. The present methodology resulted in various derivatives of 2,3-dihydroquinazoline-4(1H)-one in