16313-85-2

Usage

Uses

Used in Pharmaceutical Industry:
2,3-dihydro-2-(2-nitrophenyl)quinazolin-4(1H)-one is used as an antiparasitic agent for treating conditions such as giardiasis and cryptosporidiosis. It is effective due to its ability to interfere with the metabolic processes essential for the survival of these parasites.
Used in Antiviral Applications:
In the field of antiviral therapy, 2,3-dihydro-2-(2-nitrophenyl)quinazolin-4(1H)-one is utilized for treating viral gastroenteritis. Its potential extends to other respiratory viral infections, including influenza, although the specific antiviral mechanisms are under ongoing investigation.
Used in Research and Development:
Nitazoxanide is also used as a subject of research for further exploration of its antiviral properties and to identify additional applications in medical science, given its demonstrated effectiveness and safety.

Upstream product

• 118-48-9 isatoic anhydride 
• 552-89-6 2-nitro-benzaldehyde 
• 28144-70-9 anthranilic acid amide 
• 1885-29-6 anthranilic acid nitrile 
• 16285-03-3 2-<2-Nitro-benzylidenamino>-benzamid 

Downstream Products

• 36567-87-0 2-(2'-nitrophenyl)-4(3H)-quinazolinone 
• 16285-31-7 2-(2-aminophenyl)-2,3-dihydroquinazolin-4(1H)-one 

Relevant academic research and scientific papers

Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones

An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO3H). Herein, we have demonstrated the synthesis of these profoundly demanding N-heterocyclic molecules within 3-10 min in excellent yields at room temperature using the environmentally benign solvent ethanol. Outstanding catalytic performance, ease of retrievability, high turnover frequency (TOF) values (197.13-403.23 h?1), admirable green chemistry metrices, such as theEfactor (0.10), reaction mass efficiency (RME) value (90.9%), carbon efficiency (100%) and atom economy (AE) value (92.6%), and reusability for up to six runs without a significant loss of activity, make the current methodology advantageous from an environmental, as well as industrial perspective.

One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.

Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions

Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]

Anchoring of Cu–dimethylglyoxime complex in MCM-41 matrix: a new, recyclable, and highly efficient nanocatalyst for the green preparation of 2,3-dihydroquinazolin-4(1H)-ones

A new heterogeneous nanocatalyst containing Cu–dimethylglyoxime complex grafted to an MCM-41 matrix was synthesized. This recoverable nanocomposite was applied as a highly effective, green, thermally stable catalyst in the one-pot reductive cyclization of aromatic aldehydes with 2-aminobenzamide. 2,3-Dihydroquinazolin-4(1H)-ones were obtained in 80–98% yield. The MCM-41-silylcyclopropyl-dimethylglyoxime-Cu heterogeneous nanocomposite was well identified using X‐ray diffraction, field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy‐dispersive X‐ray spectroscopy, Brunauer–Emmett–Teller technique, and thermogravimetric analysis. The eco-friendly nanocatalyst demonstrated excellent recyclability: it could be reused for at least six successive cycles without any notable decrease in its catalytic function. Graphic abstract: [Figure not available: see fulltext.]

Mukaiyama's reagent promoted mild protocol for one-pot metal-free synthesis of dihydro quinazolinones

We have developed a fast and convenient method to prepare dihydroquinazolin-4(1H)-ones from anthranilamide and different aromatic aldehydes by using the Mukaiyama reagent. The reactions proceeded smoothly with a broad scope of substrates providing the expected products in good to excellent yields under with a low environmental factor and high atom economy. The metal-free condition and the ease of product isolation are the highlighted advantages in solving the issue of trace metal contamination in synthesized pharmaceuticals.

A novel magnetic nanocatalyst Fe3O4@PEG–Ni for the green synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Ni-PEG (polyethylene glycol) complex supported on magnetic nanoparticle was created by grafting. The catalytic activity of Fe3O4@PEG–Ni was explored through one-pot green synthesis of 2,3-dihydroquinazolin-4(1H)-ones and used as an efficient and recoverable nanocatalyst. FT-IR, XRD, EDS, BET, TGA, VSM and SEM techniques were employed to specify the nanocatalyst. This heterogeneous nanocatalyst demonstrated acceptable recyclability and could be reused several times with no considerable loss of its catalytic activity.

Synthesis and characterization of VO–vanillin complex immobilized on MCM-41 and its facile catalytic application in the sulfoxidation reaction, and synthesis of 2,3-dihydroquinazolin-4(1H)-ones and disulfides in green media

In this work, a vanillin complex is immobilized onto MCM-41 and characterized by FT-IR, X-ray diffraction, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and BET techniques. This supported Schiff base complex was found to be an efficient and recoverable catalyst for the chemoselective oxidation of sulfides into sulfoxides and thiols into their corresponding disulfides (using hydrogen peroxide as a green oxidant) and also a suitable catalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in water at 90°C. Using this protocol, we show that a variety of disulfides, sulfoxides, and 2,3-dihydroquinazolin-4(1H)-one derivatives can be synthesized in green conditions. The catalyst can be recovered and recycled for further reactions without appreciable loss of catalytic performance.

Fe3O4@MCM-41@Zn-Arg: as a novel, magnetically recoverable and ecofriendly nanocatalyst for the synthesis of disulfides, sulfoxides and 2,3-dihydroquinazolin?4(1H)?ones

The direct supporting of Zn-arginine complex on magnetic core-shell nanostructures (Fe3O4@MCM-41@Zn-Arg) was reported as a novel, heterogeneous and excellent nanocatalyst, which applied for the oxidation reaction of sulfides to sulfoxides, oxidative coupling of thiols to their corresponding disulfides and the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under mild conditions. The structure of the catalyst was studied by X-Ray diffraction, Fourier transform-infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, atomic absorption spectroscopy, and vibrating sample magnetometry techniques. The simple experimental procedure, very good catalytic activity, low cost, and excellent recycling are the noteworthy features of the currently employed heterogeneous catalytic system.

Praseodymium(iii) anchored on CoFe2O4 MNPs: An efficient heterogeneous magnetic nanocatalyst for one-pot, multi-component domino synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1: H)-one derivatives

In the present study, a facile technique to immobilize praseodymium(iii) complex on the surface of magnetic nanoparticles by using available materials is reported. The prepared samples were characterized by chemical and physical methods such as FTIR, SEM, XRD and EDX and were tested in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives. It was observed that the yields of the reactions in the presence of the prepared nanocatalyst were good to excellent. More importantly, the use of a recoverable and novel magnetic nanocatalyst in these reactions is the outstanding feature of this protocol.

A Facile Microwave and SnCl2Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones

An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17-99 %. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels-Alder addition. As a result, thiophene afforded high yields (80 %) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.