22686-80-2Relevant articles and documents
Green synthesis method and application of quinazolinone compound
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Paragraph 0032; 0043-0044; 0047, (2021/04/07)
The invention discloses a green synthesis method and application of a quinazolinone compound. The structure of the quinazolinone compound is shown as a formula I, the preparation method comprises the following steps: by taking an R1-substituted hexafluoroisopropanol 2-aminobenzoate compound and R2-substituted amidine hydrochloride as raw materials, alkali as an additive, and acetonitrile, dioxane, tetrahydrofuran, DMSO (dimethylsulfoxide) or DMF (dimethyl formamide) as a solvent, reacting at normal temperature to generate the quinazolinone compound shown in the formula I. The method provided by the invention has the advantages of no need of heating, no need of using a metal catalyst, mild reaction conditions, no generation of by-products in the reaction, 100% conversion of the raw materials and simple post-treatment process, can be used to obtain the high-purity quinazolinone product, and is a simple green synthesis method; and the quinazolinone compound has high antitumor activity, and can be used for preparing antitumor drugs.
Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature
Chen, Jiewen,Liang, En,Shi, Jie,Wu, Yinrong,Wen, Kangmei,Yao, Xingang,Tang, Xiaodong
, p. 4966 - 4970 (2021/02/06)
Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature
Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
, p. 3160 - 3170 (2019/08/07)
A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
Visible-light-mediated reaction: Synthesis of quinazolinones from 1,2-dihydroquinazoline 3-oxides
Wu, Chun-Ku,Yang, Ding-Yah
, p. 65988 - 65994 (2016/07/26)
1-Methyl-2-phenylquinazolin-4(1H)-ones were synthesized in good yield by exposing 1,4-dimethyl-2-phenyl-1,2-dihydroquinazoline 3-oxides or 1-methyl-2-phenyl-1,2-dihydroquinazoline 3-oxides to visible light in acetonitrile in the absence of any external ph
Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: A strategy to construct quinazolinones
Hikawa, Hidemasa,Ino, Yukari,Suzuki, Hideharu,Yokoyama, Yuusaku
experimental part, p. 7046 - 7051 (2012/10/07)
A novel method for the synthesis of 4-phenylquinazolinones via a palladium-catalyzed domino reaction of o-aminobenzamides with benzyl alcohols is developed. This protocol involves N-benzylation, benzylic C-H amidation, and dehydrogenation in water, which may play an important role in the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
Kinetics and mechanism of the base-catalysed cyclisation of 2-(substituted benzoylamino)benzamides giving quinazolin-4-one and quinazolin-4-thione derivatives
Hanusek, Jiri,Sedlak, Milos,Simunek, Petr,Sterba, Vojeslav
, p. 1855 - 1863 (2007/10/03)
Acylation of 2-aminobenzamide and 2-(methylamino)benzamide with substituted benzoyl chlorides in acetone has been used to prepare the respective 2-(substituted benzoylamino)benzamides 1a-i, which were then subjected to sodium methoxide catalysed ring closure to give the respective 2-(substituted phenyl)quinazolin-4 -ones 2a-i. The kinetics of the cyclisation reactions were monitored by UV/Vis spectroscopy at 25 °C in methanolic solutions of sodium methoxide. In the case of 2-(substituted benzoylamino)benzamides 1a-i and 2-(substituted benzoylamino)thiobenzamides 3a-j, non-linear dependences of observed rate constants κobs on the sodium methoxide concentrations were obtained, the shape of them being typical of a reaction with rapid pre- equilibrium. All the cyclisation reactions satisfactorily obeyed the Hammett correlation. In the case of 2 - [(benzoyl) (methyl) amino] benzamides 1e-i, increasing sodium methoxide concentration resulted in a progressive increase in κobs values which is probably due to formation of dianion. In the case of 2-(substituted benzoylamino)thiobenzamides 3b and 3h, which differ in the presence of a methyl group on the nitrogen atom the values of the activation Gibbs energy ΔG? 25 °C, activation enthalpy ΔH? 25 °C, and activation entropy ΔS? 25 °C for their respective cyclisations to 2-(substituted phenyl)quinazoline-4-thiones 4b and 4h were determined. Whereas the ΔG? 25 °C values were very close for the two substances, the ΔH? 25 °C and ΔS? 25 °C distinctly differed. This was interpreted by the enthalpy and entropy factors operating against each other in the cyclisation. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
Synthesis of substituted 2-benzoylaminothiobenzamides and their ring closure to substituted 2-phenylquinazoline-4-thiones
Hanusek, Jiri,Hejtmankova, Ludmila,Kubicova, Lenka,Sedlak, Milos
, p. 323 - 337 (2007/10/03)
Acylation of 2-aminothiobenzamide or 2-methylaminothiobenzamide with substituted benzoyl chlorides has been used to synthesise the corresponding 2-benzoyl-aminothiobenzamides whose subsequent sodium methoxide-catalysed ring closure gives the corresponding quinazoline-4-thiones. These compounds were characterised by means of their 1H- and 13C-NMR spectra. The preferred tautomeric form of selected compounds has been discussed on the basis of their 13C-NMR, IR and Raman spectra. It has been found that in the given medium 1-methyl-quinazoline-4-thiones undergo a replacement of the sulphur substituent by oxygen giving 1-methyl-quinazoline-4-ones. In strong acid media, 2-benzoylaminothiobenzamide is cyclised through its sulphur atom to give 2-phenylbenzo[d-1,3]thiazin-4-one.
Bis-azaheterocycles: Part IV - Thermal and photochemical reactions of some 3,3'-bisquinazoline-4,4'-diones
Reddy, P. S. N.,Bhavani, A. K. D.
, p. 683 - 685 (2007/10/02)
Pyrolysis of 2,2'-di(2-chlorophenyl)-3,3'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (1) at 270 deg C gives 2-(2-chlorophenyl)-1,2-dihydro-4(3H)-quinazolinone (4) and 2-(2-chlorophenyl)-4(3H)-quinazolinone (5).Similarly the pyrolysis of 2,2'-diaryl-1,1'-dimethyl-3,3'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (2a, Ar=phenyl, 2b, Ar=4-methoxyphenyl) yields 2-aryl-1-methyl-1,2-dihydro-4-(3H)-quinazolinone (6a/6b) and 2-aryl-1-methyl-4-(3H)-quinazolinone (7a/7b) along with a dimeric compound 3,3'-diaryl-1,1'-dimethyl-2,2'-bis(1,2,3,4-tetrahydroquinazoline)-4,4'-dione (8a/8b).However, thermolysis of 3,3'-bis(spiro-4'(3'H)-one) (3) at 275 deg C affords 2,5-di(2-aminophenyl)-1,3,4-oxadiazole (9) and 1,2,3,4-tetrahydro-9(10H)acridinone (10).Photolysis of 1, 2a, 2b and 3 furnishes the products 5, 7a, 7b and spiro-4'(3'H)-one (11) respectively.
Mechanism of alkaline cyclization of 2-(substituted benzamido)benzamides to 4-quinazolinones
Gardner,Kanagasooriam,Smyth,Williams
, p. 6245 - 6250 (2007/10/02)
The title amides cyclize rapidly to the corresponding quinazolin-4-ones in aqueous alkaline solution at 25°C; the pseudo-first-order rate constants fit the empirical equation k(obs) = k(max) [OH-]/(K(m) + [OH-] + [OH-]sup
