939966-50-4

Upstream product

• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 2393-23-9 4-methoxy-benzylamine 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-58-3 phenylmagnesium bromide 
• 1437798-55-4 4-(4-methoxybenzyl)-3,5-diphenyl-4,5-dihydro-1,2,4-oxadiazole 
• 31490-38-7 N-(4-methoxybenzyl)benzaldimine 
• 698-16-8 benzohydroximoyl chloride 
• 1508262-38-1 N-N-(4-methoxybenzyl)-N-(phenyl((pivaloyloxy)imino)methyl)benzamide 
• 221539-30-6 2-amino-N-(4-methoxybenzyl)benzamide 
• 98-88-4 benzoyl chloride 
• 134-20-3 2-carbomethoxyaniline 
• 121998-76-3 2-phenyl-2,3-dihydro-4(1H)-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.

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.

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

Copper-catalyzed redox-neutral C-H amination with amidoximes

CuI-catalyzed reactions of N-alkylamidoximes afforded dihydroimidazoles via sp3 C-H amination. On the other hand, the reactions of N-benzoylamidoximes resulted in sp2 C-H amination to form quinazolinones. The reaction mechanisms could be characterized as a redox-neutral radical pathway including a Cu(i)-Cu(ii) redox catalytic cycle. The Royal Society of Chemistry.

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

Functionalized carbodiimide mediated synthesis of 2,3-disubstituted quinazolin-4(3 H)-ones via the tandem strategy of C-nucleophilic addition and intramolecular NH-substitution cyclization

A facile synthesis of quinazolin-4(3H)-ones possessing carbon substituents at positions 2 and 3 has been developed. Key to the synthesis is a tandem strategy involving introduction of a 2-substituent and construction of the quinazolinone framework via C-nucleophilic addition to the carbodiimide cumulenic carbon followed by intramolecular nucleophilic substitution by the newly formed NH moiety at the proximal ester group.

One-pot three-component synthesis of 4(3 H)-quinazolinones from benzyl halides, isatoic anhydride, and primary amines

A novel, one-pot, and three-component synthesis of 4(3H)-quinazolinones is described. Benzyl halides are oxidized to aldehydes under mild Kornblum conditions then undergo a three-component reaction with isatoic anhydride and primary amines to produce 4(3H)-quinazolinones in excellent yields. Georg Thieme Verlag Stuttgart. New York.