459796-19-1

Upstream product

• 28144-70-9 anthranilic acid amide 
• 1759-53-1 cyclopropanecarboxylic acid 
• 57297-29-7 cyclopropylcarboxamidine hydrochloride 
• 88-65-3 2-bromobenzoic-acid 
• 88-67-5 2-Iodobenzoic acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 219689-52-8 2-amino-N-(cyclopropylmethyl)benzamide 
• 118-48-9 isatoic anhydride 
• 4023-34-1 cyclopropanecarboxylic acid chloride 
• 1885-29-6 anthranilic acid nitrile 
• 91-56-5 indole-2,3-dione 
• 24922-02-9 Ethyl 3-cyclopropyl-3-oxopropionate 
• 2516-33-8 Cyclopropylmethanol 

Downstream Products

• 898044-61-6 C₁₁H₉ClN₂ 

Relevant academic research and scientific papers

Straightforward synthesis of quinazolin-4(3: H)-ones via visible light-induced condensation cyclization

A green, simple and efficient method is developed for the synthesis of quinazolin-4(3H)-ones via visible light-induced condensation cyclization of 2-aminobenzamides and aldehydes under visible light irradiation. The reaction proceeds using fluorescein as a photocatalyst in the presence of TBHP without the need for a metal catalyst. In addition, this reaction tolerates a broad scope of substrates and could afford a variety of desirable products in good to excellent yields. Thus, the present synthetic method provides a straightforward strategy for the synthesis of quinazolin-4(3H)-ones.

Method for preparing quinazolone and derivatives thereof by using chitosan-loaded copper catalyst

The invention discloses a method for preparing quinazolone and derivatives thereof by using a chitosan-loaded copper catalyst, which comprises the following steps of replacing residual gas in a reaction container with inert gas, adding a catalytic amount of copper ion-loaded chitosan catalyst, substituted 2-halogenated benzoic acid, substituted amidine hydrochloride, inorganic alkali and a mixed solvent into the reaction container, and heating for reaction, after the reaction time is 2-18 hours, extracting the product by using ethyl acetate, filtering and recovering the copper ion-loaded chitosan catalyst, concentrating the filtrate under reduced pressure, and purifying the product by column chromatography. The method has the advantages of low catalyst dosage, recoverability, easy separation after reaction, no metal residue, simple post-treatment, and suitableness for large-scale production.

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis

A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.

Synergistic catalysis on Fe-N: X sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes

In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe-Fe3C nanoparticles and Fe-Nx sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H2O2 as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe-Nx sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles.

Method for synthesizing quinazoline and quinazolinone compounds

The invention discloses a method for synthesizing quinazoline and quinazolinone compounds by oxidative coupling dehydrogenation with a nitrogen-doped hierarchical porous biomass basic carbon materialsupported catalyst. The method comprises the steps of adding 2-aminobenzylamine, 2-aminobenzamide, a formaldehyde compound R-CHO, the supported catalyst, a mixed solvent of water and tetrahydrofuran and hydrogen peroxide under a closed reaction condition, reacting at 60-140 DEG C for 6-24 hours, cooling to room temperature, filtering a reaction solution, and obtaining the quinazoline compound or the quinazolinone compound by silica gel column chromatography. The method adopts a low-cost metallic iron nanocatalyst through a 'one-pot' series reaction which is a green synthetic chemical strategy.Compared with a previous noble metal catalyst system, the reaction system is simple in operation, mild in condition and low in cost, and is favorable for large-scale production and industrial application.

Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles

A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.

A quinazolinone of heterocyclic compound synthetic method

The invention discloses a quinazolinone of heterocyclic compound synthetic method. In under the action of the water-soluble alkali using air as the oxidizing agent, and ortho-amino alcohol oxidation fragrant nitrile compound - cyclized - oxidation of high efficiency series reaction one-step preparation quinazolinone of heterocyclic compound synthetic method. This method does not need the use of expensive transition metal catalyst and ligand, but the use of water-soluble alkali as promoter, the alkali can be removed by water washing mode is convenient, so product transition metal-free residue, is suitable as a pharmaceutical preparation of the precursor, the method condition is simple, easy to operate, low requirement for the device, and can utilizes air as economic security green oxidizing agent, water-soluble alkali as promoter, the only by-product is water, atom economical high, has a certain research and industrial application prospect.

One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies

A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).

Phosphorous acid functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment for one-pot C-C and C-N bond formation reactions

The preparation and application of fiber catalysts have attracted much attention. However, research on the effect of the micro-environment of fiber catalysts on the catalytic activities though of special importance is limited. In this work, a novel strategy for the synthesis of phosphoric acid-functionalized polyacrylonitrile fibers with a polarity tunable surface micro-environment by hydrophobic groups for one-pot C-C and C-N bond formation reactions is reported. The special hydrophobic surface micro-environment of the fiber catalysts is proven to promote the catalytic activities impressively in cyclocondensation of β-ketoesters with 2-aminobenzamides, the Knoevenagel condensation as well as the multi-component Biginelli reactions in green solvents. Both the surface synergy of the catalytic sites and hydrophobic auxiliary groups (benzyl or n-butyl) in the surface of fiber catalysts and interface acceleration in reaction medium play an important role in the highly efficient promotion of catalytic activity. Thereby a surface synergistic mechanism is proposed to explain the micro-environment effect. In addition, the fiber catalysts could be simply separated from the reaction system using tweezers and directly used in the next cycle without further treatment. Importantly, even after 10 reaction cycles in water or ethanol, there is no significant loss in their catalytic activity. The results indicate that the phosphoric acid functionalized fibers show green and sustainable potential for industrial production.

Ultrasound-promoted synthesis of 4(3H)-quinazolines under Yb(OTf)3 catalysis

A novel method to perform the Niementowski reaction leading to 4(3H)-quinazolines is reported. The 4(3H)-quinazolines were obtained in good to excellent yields by microwave irradiation or ultrasound-assisted synthesis from 2-aminobenzonitrile and acyl chlorides in solvent-free conditions and in the presence of Yb(OTf)3 (10 mol%). Ultrasound-based methodology performed better than the microwave-assisted process in terms of yields for all examples. The procedure reported herein represents also the first reported example of an ultrasound-promoted Niementowski-like reaction. (Chemical Equation Presented).