85094-66-2

Upstream product

• 100-66-3 methoxybenzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 316362-07-9 3-benzyl-2-benzylsulfanyl-3H-quinazolin-4-one 
• 1437798-49-6 4-benzyl-3-(4-methoxyphenyl)-5-phenyl-4,5-dihydro-1,2,4-oxadiazole 
• 780-25-6 N-benzylidene benzylamine 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 122022-10-0 2,3-dihydro-2-(4-methoxyphenyl)-4(1H)-quinazolinone 
• 118-48-9 isatoic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 5471-20-5 2-amino-N-benzylbenzamide 
• 623-12-1 4-chloromethoxybenzene 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 82082-50-6 N-benzyl-2-bromobenzamide 

Downstream Products

• 89860-51-5 2-(4-hydroxyphenyl)-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives

Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.

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

Ligand-Free Pd-Catalyzed and Copper-Assisted C-H Arylation of Quinazolin-4-ones with Aryl Iodides under Microwave Heating

A microwave-assisted method for the palladium-catalyzed direct arylation of quinazolin-4-one has been developed under copper-assistance. This method is applicable to a wide range of aryl iodides and substituted (2H)-quinazolin-4-ones. This protocol provides a simple and efficient way to synthesize biologically relevant 2-arylquinazolin-4-one backbones.

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

Rapid assembly of quinazolinone scaffold via copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia: Application to the synthesis of the alkaloid tryptanthrin

An efficient and practical procedure for the preparation of 2-substituted and 2,3-disubstituted quinazolinones was achieved through copper-catalyzed tandem reaction of 2-bromobenzamides with aldehydes and aqueous ammonia under air. Control experimental results indicated that this tandem reaction is triggered by a copper-catalyzed direct amination of 2-bromobenzamides with aqueous ammonia, followed by cyclocondensation and oxidative aromatization. As an application, this novel methodology provides a concise and practical one-pot route to the synthesis of alkaloid tryptanthrin. This journal is

Syntheses of quinazolinones from 2-iodobenzamides and enaminones via copper-catalyzed domino reactions

N-Substituted 2-iodobenzamides and enaminones undergo cascade transformations to achieve quinazolinones via a copper-catalyzed Ullmann-type coupling, a Michael addition and a retro-Mannich reaction. A unique stereochemical feature of this domino process was that Z-enaminones reacted without external ligands, whereas E-enaminones required the assistance of ligands. This journal is

Oxidative radical skeletal rearrangement induced by molecular oxygen: Synthesis of quinazolinones

Oxidative skeletal rearrangement of 5-aryl-4,5-dihydro-1,2,4-oxadiazoles into quinazolinones is induced by molecular oxygen (under a dry air atmosphere) that likely proceeds via transient iminyl radical species. Concise syntheses of biologically active qu

Modular access to heterocycles: Methyl 3-aminobenzo[b]thiophene-2- carboxylate-thiourea linkage or pyrimidine-4-one-2-thione formation

Modular conditions for the formation of thioureas or pyrimidine-4-one-2- thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-l-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.

Synthesis of 4(3H)-Quinazolinones from Derivatives of Methyl 2-Isothiocyanatobenzoate

Ethyl N-((2-methoxycarbonylphenyl)thiocarbamate (2), N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide (3b), and 2-(4-methoxyphenyl)4H,-3,1-benzothiazin-4-one (4a), react with nucleophilic reagents containing at least one primary amino group to yield a variety of 2-substituted and 2,4-disubstituted 4(3H)-quinazolinones, as well as some tricyclic and tetracyclic products.