1022-45-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 359, 1973 DOI: 10.1016/S0040-4039(01)95661-8Chemical and Pharmaceutical Bulletin, 24, p. 1197, 1976 DOI: 10.1248/cpb.24.1197Journal of the American Chemical Society, 86, p. 2086, 1964 DOI: 10.1021/ja01064a048

InChI:InChI=1/C14H10N2O/c17-14-11-8-4-5-9-12(11)15-13(16-14)10-6-2-1-3-7-10/h1-9H,(H,15,16,17)

Upstream product

• 118-48-9 isatoic anhydride 
• 7035-69-0 N-(4-chlorophenyl)benzamidine 
• 825-60-5 benzimidic acid ethyl ester 
• 4676-99-7 2-phenyl-indol-3-one oxime 
• 118-92-3 anthranilic acid 
• 1670-14-0 benzamidine monohydrochloride 
• 2227-79-4 benzenecarbothioamide 
• 134-20-3 2-carbomethoxyaniline 
• 7471-86-5 methyl benzimidate 
• 579-93-1 2-(Benzoylamino)benzoic Acid 
• 57-13-6 urea 
• 888-71-1 3,5-diphenyl-1,2,4-oxadiazole 
• 90-16-4 1,2,3-benzotriazin-4(3H)-one 
• 100-47-0 benzonitrile 

Downstream Products

• 109812-05-7 3-(2,3-dihydroxy-propyl)-2-phenyl-3H-quinazolin-4-one 
• 6483-99-4 2-phenyl-3,4-dihydroquinazolin-4-thione 
• 6484-25-9 4-chloro-2-phenylquinazoline 
• 115765-01-0 3-(N'-phenylamido)-2-phenyl-4(3H)-quinazolinone 
• 115765-02-1 3-(N'-phenylthioamido)-2-phenyl-4(3H)-quinazolinone 
• 503856-78-8 4-(4-chlorobutoxy)-2-phenylquinazoline 
• 503856-76-6 4-(2-chloroethoxy)-2-phenylquinazoline 
• 76315-66-7 3-(2-chloroethyl)-2-phenylquinazolin-4(3H)-one 
• 503856-77-7 4-(3-chloropropoxy)-2-phenylquinazoline 
• 503856-72-2 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one 
• 77651-75-3 butyl-(2-phenyl-quinazolin-4-yl)-amine 
• 1257629-14-3 C₂₀H₁₆N₄O₃ 
• 1257629-16-5 4-(1,3,4-oxadiazol-2-ylmethoxy)-2-phenylquinazoline 
• 1257629-19-8 5-{[(2-phenylquinazolin-4-yl)oxy]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione 

Relevant academic research and scientific papers

Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues

A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.

Palladium Catalyzed Cross-Dehydrogenative Coupling/Annulation Reaction: A Practical and Efficient Approach to Hydroxyisoindolo[1,2-b]quinazolinone

The palladium-catalyzed cross-dehydrogenative coupling (CDC) followed by an intramolecular cyclization between arylquinazolinones and aldehydes has been described. This viable transformation provides a variety of novel substituted hydroxyisoindolo[1,2-b]quinazolinone compounds in moderate to good yields. Additionally, the reaction is performed with toluene in place of benzaldehyde by using an excess amount of tert-butyl hydroperoxide (TBHP) as the oxidant in good yield.

A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones

This paper describes the synthesis of 2-substituted and 2,3-disubstituted 4(3H)-quinazolinones via a tandem reaction involving anthranilamides and aromatic aldehydes catalyzed by 3 mol% CuO powder under air atmosphere. This new method has several advantages: it uses recyclable and cheap CuO powder as the catalyst and air as the green oxidant, water is the only byproduct, and the solvent is recycled. It is easy to run, has a high atom economy and good to excellent yields. A mechanism for the CuO-catalyzed synthesis of the 4(3H)-quinazolinones is proposed.

Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones

2-Arylquinazolin-4(3H)-ones 1-25 were synthesized by reacting anthranilamide with various benzaldehydes using CuCl2·2H 2O as a catalyst in ethanol under reflux. Synthetic 2-arylquinazolin-4(3H)-ones 1-25 were evaluated for their β-glucuronidase inhibitory potential. A trend of inhibition IC50 against the enzyme in the range of 0.6-198.2 μM, was observed and compared with the standard d-saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Compounds 13, 19, 4, 12, 14, 22, 23, 25, 15, 8, 17, 11, 21, 1, 3, 18, 9, 2, and 24 with the IC50 values within the range of 0.6-44.0 μM, indicated that the compounds have superior activity than the standard. The compounds showed no cytotoxic effects against PC-3 cells. A structure-activity relationship is established.

Cp2ZrCl2-catalyzed synthesis of 2-substituted quinozolin-4(3H)-ones

Zirconocene dichloride (Cp2ZrCl2) in the presence of DMF was found to be a highly efficient catalyst for the synthesis of structurally diverse 2-substituted quinozolin-4(3H)-ones by reaction of anthranilimide with a wide range of aryl aldehydes. Copyright

Ligand-Free Copper-Manganese Spinel Oxide-Catalyzed Tandem One-Pot C–H Amidation and N-Arylation of Benzylamines: A Facile Access to 2-Arylquinazolin-4(3H)-ones

An efficient ligand-free copper-manganese (Cu-Mn) spinel oxide-catalyzed direct tandem C?H oxygenation and N-arylation of benzylamines has been developed. The method has been utilized for the synthesis of medicinally important 2-arylquinazolin-4(3H)-ones. Salient features of this method include recyclable catalyst, no ligand, excellent product yields, shorter reaction times and a broad substrate scope. (Figure presented.).

Site-Selective C–H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates

The site-selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)-catalyzed C–H amidation of 2-aryl quinazolin-4(3H)-ones with a range of nitrene surrogates including dioxazolones, organic azides, and N-methoxyamides. Complete site-selectivity and functional group tolerance are observed. Notably, the large-scale reaction and late-stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.

Electron transfer-induced oxidation of 2,3-dihydroquinazolin-4(1H)-ones

A series of 2-substituted 2,3-dihydroquinazolin- 4(1H)-ones were oxidized to quinazolin-4(3H)-ones using tetrabutylammonium peroxydisulfate. The rate and the outcome of the reaction are dependent on the type and nature of 2-substitution. An electron transfer mechanism is proposed for this study, which is supported by the retention or elimination of 2-substitution during the oxidation process.

A novel method for the synthesis of 4(3H)-quinazolinones

Condensation of anthranilamide with aryl, alkyl or heteroaryl aldehydes in refluxing ethanol and the presence of CuCl2 afforded the corresponding 2-substituted quinazolinones in excellent yields.

Q-Tube assisted MCRs for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones

A Q-tube assisted, efficient method for the preparation of 2-phenylquinazolin-4-ones is here presented. The target structures were prepared through the one-pot, multicomponent reaction between isatoic anhydride, an aromatic aldehyde and a primary amine following a catalyst-free approach. The use of the commercially available Q-tube apparatus allowed to perform reactions at external temperature higher to the solvent boiling point generating medium pressure conditions, shortening the reaction times and affording good yields in all the example herein reported. Formula parented.