37856-14-7

Upstream product

• 118-48-9 isatoic anhydride 
• 106-49-0 p-toluidine 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 32212-38-7 2-amino-N-(4-methylphenyl)benzamide 
• 1663-61-2 triethoxymethylbenzene 
• 94871-76-8 2-benzoylamino-N-(4-methylphenyl)benzamide 
• 118-92-3 anthranilic acid 
• 98-88-4 benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 15999-95-8 4-methylphenylbenzimidoyl chloride 
• 100-52-7 benzaldehyde 
• 108-86-1 bromobenzene 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 

Downstream Products

• 49699-38-9 2-phenyl-3-p-tolyl-3H-quinazoline-4-thione 

Relevant academic research and scientific papers

Complementary Reactivity in Selective Radical Processes: Electrochemistry of Oxadiazolines to Quinazolinones

Electrochemistry has recently emerged as a sustainable approach for efficiently generating radical intermediates utilizing eco-friendly electric energy. An electrochemical process was developed to transform 1,2,4-oxadiazolines under mild conditions. The electrochemical N-O bond cleavage at a controlled oxidation potential led to the selective synthesis of quinazolinone derivatives that could not be obtained by photocatalytic radical processes, indicating complementary reactivities in radical processes. The electrochemical reaction pathways were fully revealed by density functional theory-based investigations.

α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocyclesviadecarboxylative oxidative annulation reaction

A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include thein situgeneration of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.

Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation

One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone.

Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone

The invention discloses a method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone. According to the method, heteropolyacid ion liquid is taken as a catalyst, microwave heating and solvent-free synthesis technologies are utilized, and dihydroquinazolinone and quinazolinone derivatives are selectively synthesized through a 'one-pot-method' synthetic strategy with isatoic anhydride or derivatives of the isatoic anhydride, amine and aldehyde as raw materials. Compared with the prior art, the method has the multiple advantages that the efficiency is high, the costis low, environmental friendliness is realized, reaction selectivity is good, the product yield is high, selective synthesis can be realized, the catalyst is convenient to recover and apply, operationis easy, and industrial mass production is convenient, and the method is an environment-friendly efficient selective synthesis novel method and meets the environment-friendly and chemical developmentidea.

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.).

Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones

A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.

Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions

The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.

Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides

The regiospecific C-2-H arylation of N-3-substituted quinazolin-4(3H)-ones with a wide range of aryl or (hetero)aryl halides under microwave irradiation was studied. A ligand-dependent palladium/copper bicatalytic system was developed and allowed direct c

Efficient and practical one-pot route to synthesise quinazolin4(3H)-ones using trifluoromethanesulfonic anhydride and 2-chloropyridine

An effective, novel and rapid one-pot three-component route to quinazolin-4(3H)-ones from commercially available starting materials is described. Isatoic anhydride reacts with acyl chlorides and different amines using a combination of trifluoromethanesulf

One-pot solvent-free synthesis of 2, 3- disubstituted 4(3H)- quinazolinones catalyzed by long-chain double SO3H-functionalized Br?nsted acidic ionic liquids under microwave irradiation

A solvent-free approach for synthesis of 2, 3-disubstituted 4(3H)-quinazolinones by condensation of anthranilic acid with acyl chlorides and aromatic/aliphatic amines using two long chain double SO3H-functionalized acdic ionic liquids as catalyst under microwave irradiation was reported. Under optimized conditions, the reactions completed within 4-8 min and gave the target compounds in the yields of 76-94 %. Two ionic liquids could be recovered readily and recycled three times without any significant loss in their catalytic activity.