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1.
A new approach to synthesize quinazoline-4(3H)-ones was achieved by oxidation of quinazolines using peracetic acid, which possesses some advantages of economic reagents, simplified operation, high efficiency, and environmental friendliness. Application of this method allowed us to synthesize a series of quinazolin-4(3H)-ones with different substituents at 6 and 7 positions in good to excellent yields, including the key intermediates of tyrosine kinase inhibitors such as PD153035, Erlotinib, and Gefitinib. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
2.
M. R. Yadav S. T. Shirude A. Parmar R. Balaraman R. Giridhar 《Chemistry of Heterocyclic Compounds》2006,42(8):1038-1045
2,3-Diaryl-4(3H)-quinazolinones containing various substituents on diaryl rings have been synthesized and evaluated for their
cyclooxygenase-2 inhibitory activity by the colorimetric COX (ovine) inhibitor screening assay and anti-inflammatory activity
by the carrageenan-induced rat paw edema assay. 2-(4-Nitrophenyl)-3-(4-tolyl)-4(3H)-quinazolinone showed a maximum COX-2 inhibition
of 27.72% at 22 μM concentration in the present series and exhibited a mild anti-inflammatory activity at a dose of 50 mg/kg
in carrageenan-induced rat paw edema assay.
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1198–1205, August, 2006. 相似文献
3.
Chikkanti Jaganmohan Vinay Kumar K. P. Sandeep Reddy G. Sandeep Mohanty Jaydeep Kumar Venkateswara Rao B. 《合成通讯》2018,48(2):168-174
A new versatile and efficient strategy for the synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazoline-4(1H)-one compounds has been developed by one-pot multicomponent reaction with isatoic anhydride, amines followed by in situ-generated Vilsmeier reagent. The reaction has also been studied with different amines and solvents. 相似文献
4.
Anthranilonitrile reacting with formic acid at room temperature for three days gave 64% of 3-(2-cyanophenyl)quinazolin-4(3H)-one. Under similar conditions anthranilic acid. 4-nitroaniline, and 2,5-dichloroaniline were N-formylated in good yields.Institute of Organic Chemistry and Technology, Silesian Technical University, Krzywoustego, 4, 44–100 Gliwice, Poland; e-mail: wojtex@zeus.polsl.gliwice.pl. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 922–924, July, 2000. 相似文献
5.
《合成通讯》2013,43(4):735-742
Abstract An easy and generalized route to 2(3H)‐benzimidazolones, 2(3H)‐benzoxazolone and 2(3H)‐benzothiazolone is attempted. A novel one‐pot method for the in situ generation and cyclisation of ortho substituted benzoic acid azides is reported via the application of ammonium azide and Vilsmeier complex. 相似文献
6.
An efficient, ligand- and metal-oxidant-free, one-pot, cascade aerobic oxidative, palladium-catalyzed, multicomponent reaction has been developed through isocyanide insertion of less active secondary amide and aromatic amine, which leads to 2-amino-substituted-4(3H)-quinazolinones. This approach proves to be one of the simplest methods for the synthesis of this class of valuable bioactive heterocyclic scaffolds. 相似文献
7.
《Green Chemistry Letters and Reviews》2013,6(4):603-607
Abstract An efficient and convenient method for the preparation of 3-benzylquinazolin-4(1H)-one derivatives under solvent-free and catalyst-free conditions by the reaction of isatoic anhydride, benzylamine, and aromatic aldehydes was reported. In reported papers, ammonia water, ammonium salt, and aromatic amine were often used to synthesize quinazolin-4(1H)-one derivative, but benzylamine was seldom used in this synthesis. This article offers a green method for the synthesis of 3-benzylquinazolin-4(1H)-one derivative used benzylamine as starting material. This methodology has the advantages of short reaction time, mild reaction conditions, easy work-up, and environmental friendliness. 相似文献
8.
H. H. Abdel‐Razik 《中国化学会会志》2005,52(1):141-148
Several quinazoline‐2(1H),4(3H)‐dione derivatives were synthesized from pyrimidine‐2(1H),4(3H)‐dione derivative. 相似文献
9.
10.
Mohammad Mahdavi Mehdi Asadi Mina Saeedi Maryam Hosseinpour Tehrani Seyedeh Sara Mirfazli Abbas Shafiee 《合成通讯》2013,43(21):2936-2942
A series of new boron-containing quinazolinones, benzo[d][1,3,2]diazaborinin-4(1H)-one derivatives, were synthesized by the sequential one-pot reaction of isatoic anhydride, amines, and arylboronic acids in the absence of a catalyst and solvent. Heating isotoic anhydride and amines led to the formation of 2-aminobenzamide intermediates, which reacted easily with boronic acids to obtain the title compounds in good yields. Solvent-free conditions provided a unique procedure because the corresponding products were not obtained using various solvents either under reflux conditions or at room temperature. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.] 相似文献
11.
12.
Mahmoud R. Mahmoud 《合成通讯》2013,43(10):1516-1529
The title compound 1 was prepared and allowed to react with a series of nitrogen nucleophiles to afford the quinazoline and quinazolinone derivatives 2–12 and tetrazole derivative 13. The IR, 1H NMR, 13C NMR, and mass spectra of all the synthesized compounds were discussed. 相似文献
13.
Some new derivatives 7‐chloro‐2‐[2‐(2,6‐dichlorophenyl)amino]benzyl‐3‐[4‐(2‐substituted phenyl‐4‐oxo‐ thiazolidin‐3‐yl)phenyl]sulfonamido‐quinazolin‐4(3H)‐ones 5a – 5l were synthesized from 2‐[2‐(2,6‐dichloro‐phenyl)amino]phenyl acetic acid via acid chloride, benzoxazinone, amino quinazolin‐4(3H)‐one and Schiff base formation. The synthesized compounds were screened for in vitro antibacterial and antifungal activities by broth micro dilution method. Some of the Schiff base as well as 4‐thiazolidinone derivatives showed promising antibacterial activity while pronounced antifungal activity was observed against C. albicans. 相似文献
14.
15.
Hexamethyldisilazane-mediated reaction of quinazolin-4(3H)-ones with primary amines led to facile formation of 4-aminoquinazolines through tandem silylation and substitution in a single pot. Excellent yields of the products (83–97%) and environmental friendliness (avoiding the use of chlorination reagents) are the advantages of this method. 相似文献
16.
3-苯基喹唑啉-4(3H)-酮的合成及晶体结构 总被引:1,自引:0,他引:1
标题化合物C14H10ON2是由邻硝基苯甲酰苯胺与原甲酸三乙酯在低价钛试剂作用下反应而得。结构通过单晶X-射线衍射分析确定, 其晶体属于单斜晶系, 空间群P21/c, a = 12.080(2), b = 7.793(1), c = 11.599(1) ? b = 97.56(1), Mr = 222.24, V = 1082.4(2) ?, Dc = 1.364 g/cm3, Z = 4, m(MoKa) = 0.88 mm-1, F(000) = 464, R = 0.0385, wR = 0.0851。X-衍射分析表明: 平面I (C(1)~C(6))与平面II (C(9)~C(14))之间的夹角为124.38; 平面I与平面III (ON(1)?N(2)C(7)C(8)C(9)C(14))之间的两面角为125.47; 平面II与平面III之间的两面角为2.76。 相似文献
17.
Controlling selectivity of the reactions of aromatic aldehydes and 2-aminobenzamide in ionic liquid catalyzed by iodine at either room temperature or at 80 °C under nitrogen resulted in the synthesis of (E)-Schiff bases, 2,3-dihydro-2-arylquinazolin-4(1H)-one and 2-arylquinazolin-4(3H)-one derivatives, in excellent yields. 相似文献
18.
<正>A series of novel unsymmetrical N-(4-oxo-2-phenyl-3(4H)-quinazolinoyl)-N-(aryl) acetamidines was synthesized by reacting ethyl(1H)-N-(4-oxo-2-phenylquinazolin-3(4H)-y1)ethanimidoate(2) and suitable reactive aromatic amines.Structures' determination of the synthesized compounds was carried out using spectroscopic techniques including IR,~1H NMR,and mass spectrometry. Structural effects on reactivity were also studied. 相似文献
19.
P. Paradesi Naidu Akula Raghunadh K. Raghavendra Rao Ramamohan Mekala J. Moses Babu B. R. Rao 《合成通讯》2014,44(10):1475-1482
Urea/thiourea have been identified as an effective ammonia surrogate in the construction of quinazolin-4(3H)-one ring. This strategy afforded a simple and catalyst-free synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones via the reaction of isatoic anhydride and aryl aldehydes in the presence of urea or thiourea in ethanol. The reaction proceeded well to afford the quinazolin-4(3H)-one or its dihydro derivative, depending on the nature of carbonyl compounds employed. 相似文献
20.
Tatyana N. Moshkina Emiliya V. Nosova Julia V. Permyakova Galina N. Lipunova Ekaterina F. Zhilina Grigory A. Kim Pavel A. Slepukhin Valery N. Charushin 《Molecules (Basel, Switzerland)》2022,27(21)
Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3H)-ones and 4-cyano-2-arylquinazolines with Et2N-, Ph2N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3H)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3H)-one. Moreover, triphenylamino derivative based on quinazolin-4(3H)-one with para-phenylene linker displays the highest quantum yield of 40% in powder. The fluorescence QY of Et2N and Ph2N derivatives decrease when going from toluene to MeCN solution, whereas carbazol-9-yl counterparts demonstrate strengthening of intensity that emphasizes the strong influence of donor fragment nature on photophysical properties. 4-Cyanoquinazolines are less emissive in both solvents, as well as, in solid state. The introduction of cyano group into position 4 leads to orange/red colored powder and dual emission bands. Some molecules demonstrate the increase in emission intensity upon addition of water to MeCN solution. According to frontier molecular orbitals (HOMO, LUMO) calculations, the energy gap of 4-cyanoquinazoline decreases by more than 1 eV compared to quinazolin-4-one, that is consistent with experimental data. 相似文献