67796-16-1

Upstream product

• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 109-73-9 N-butylamine 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 41182-88-1 N-butyl-benzimidoyl chloride 
• 552-89-6 2-nitro-benzaldehyde 
• 82743-97-3 N-butyl-N'-hydroxybenzimidamide 
• 1508263-00-0 N-butyl-N'-(pivaloyloxy)benzimidamide 
• 698-16-8 benzohydroximoyl chloride 
• 1508262-39-2 N-butyl-N-(phenyl((pivaloyloxy)imino)methyl)benzamide 
• 27895-78-9 N-butyl-1-(2-nitrophenyl)methanimine 
• 98-88-4 benzoyl chloride 
• 134-20-3 2-carbomethoxyaniline 

Relevant academic research and scientific papers

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water

We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).

Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α?keto acids with 2-aminobenzamides

Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α?keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction conditions (room temperature and air atmosphere), and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.

Method for synthesizing quinazolinone compound under photocatalysis condition

The invention belongs to the technical field of compound preparation. The invention discloses a method for synthesizing a quinazolinone compound under a photocatalysis condition. The method comprisesthe following step: by taking a compound shown as a formula I and a compound shown as a formula II as raw materials and copper salt or nickel salt or iron salt as a catalyst, performing a cyclizationreaction in a nitrogen atmosphere, an illumination condition, an oxygen atmosphere and an illumination condition in sequence under the action of an alkali and a solvent to synthesize the quinazolinonecompound shown as a formula III. According to the method, under the illumination condition, o-halogen benzamide can not only react with fatty amine, but also react with benzylamine to obtain the quinazolinone compound.

Synthesis of Quinazolin-4(3 H)-ones via the Reaction of 2-Halobenzamides with Nitriles

This paper describes a convenient method to synthesize quinazolin-4(3H)-ones from simple and readily available 2-halobenzamides and nitriles. The Lewis acid Cu-catalyzed nucleophilic addition of 2-halobenzamide to nitriles followed by SNAr reaction proceeds smoothly in the presence of tBuOK as a base to produce quinazolinone derivatives.

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.).

Approach to the Synthesis of 2,3-Disubstituted-3H-quinazolin-4-ones Mediated by Ph3P-I2

Readily available N-substituted amides or their requisite carboxylic acids or acid chlorides have been used to construct 2,3-disubstituted-3H-quinazolin-4-ones in a one-pot procedure. Key transformation in this convergent approach involves Ph3P-I2-mediated formation of amidine upon condensation of an amide or the intermediate amide with methyl anthranilate. Cyclization of the amidine-tethered anthranilate then affords 2,3-disubstituted-3H-quinazolin-4-ones in good to excellent yields under mild conditions.

Pd-Catalyzed Regioselective Mono-Arylation: Quinazolinone as the Inherent Directing Group for C(sp2)-H Activation

The Pd-catalyzed quinazolinone-directed regioselective monoarylation of aromatic rings by C-H bond activation is developed. A broad substrate scope is demonstrated for both quinazolinone as well as diaryliodonium triflates. The use of a base was found to be crucial for this transformation, unlike for the known nitrogen-directed arylations. All of the novel quinazolinones of biological interest were synthesized by using the operationally simple Pd(II)-catalyzed arylation reaction.

A quinazolinone aromatic synthetic method of the compound (by machine translation)

The invention discloses a method for the synthesis of quinazolinone aromatic compounds, the 2 - aryl indole, organic amine/ammonium and cuprous bromide dissolved in organic solvent, under the condition of oxygen participation in, for 60 - 120 °C reaction 20 - 30 hours later, after the separation and purification, to get the states kuikui zuo lin the alkone aromatic compound. Synthesis method of the invention are easily available raw materials, high yield (as high as 99%); mild reaction conditions, the reaction time is short, wide substrate range, reaction specificity is strong, the after-treatment is simple and convenient and green. (by machine translation)

NHC-Catalyzed Benzylic Csp3–H Bond Activation of Alkylarenes and N-Benzylamines for the Synthesis of 3H-Quinazolin-4-ones: Experimental and Theoretical Study

An N-heterocyclic carbene catalyzed benzylic Csp3–H bond activation of alkylarenes and N-benzylamines under metal-free conditions was developed. This organocatalyzed oxidative transformation afforded the corresponding carbonyl derivatives in good to excellent yields. A variety of alkylarenes and N-benzylamines were tolerated under the optimized reaction conditions. The established method was further extended to the synthesis of biologically important 3H-quinazolin-4-ones in good yields. For example, NPS 53574, a potent calcium receptor antagonist, was successfully synthesized by using this oxidative protocol. DFT studies show that the benzylic C–H bond activation proceeds through the nucleophilic attack of the free carbene on the benzylic carbon atom.

Rhodium(II)-Catalyzed Carbenoid Insertion of N-Tosylhydrazones into Amide N-H Bonds: An Efficient Approach to N3-Benzyl/Alkyl-2-arylquinazolinones

Dirhodium(II) acetate-catalyzed reactions of N-tosylhydrazones with dihydroquinazolinones bearing different types of N-H bonds that give N3-benzyl/alkyl-2-arylquinazolin-4(3H)-ones through Csp3-N bond formation by oxidative dehydroge