- Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO
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A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.
- Wen, Simiaomiao,Du, Yifan,Liu, Yiwen,Cui, Xiaofeng,Liu, Qixing,Zhou, Haifeng
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- An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols
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An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.
- Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli
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supporting information
p. 15344 - 15349
(2021/09/07)
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- Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes
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A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.
- Zhang, Xiangyu,Luo, Chujun,Chen, Xiaoyong,Ma, Weilin,Li, Bin,Lin, Zirui,Chen, Xiuwen,Li, Yibiao,Xie, Feng
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- Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones
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In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.
- Wang, Rongzhou,Liu, Shiyuan,Li, Longfei,Song, Ao,Yu, Shengsheng,Zhuo, Shuping,Xing, Ling-Bao
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- Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
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The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.
- Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli
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supporting information
p. 4446 - 4450
(2021/06/30)
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- Method for preparing N - heterocyclic ring through visible light mediated dehydrogenation
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The invention discloses a method for preparing N - heterocyclic rings through visible light mediated dehydrogenation, and the reaction can be carried out under the conditions of room temperature and visible light without heating. The novel tetra-coordination N-N - diaryl chelating borate compound serves as a photocatalyst, so that the use of a noble metal photocatalyst is avoided, precious metal residue in the reaction product can be reduced as much as possible, and the method is more suitable for synthesizing bioactive molecules.
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Paragraph 0098-0103
(2021/10/02)
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- Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
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A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
- Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
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p. 1496 - 1501
(2021/05/03)
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- Method for photocatalytic synthesis of quinazolinone
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The invention discloses a method for photocatalytic synthesis of quinazolinone. Anthranilamide and aldehyde are used as raw materials, fluorescein is used as a photocatalyst, p-toluene sulfonic acid is used as an auxiliary catalyst, and the quinazolinone is obtained through photocatalytic reaction under the irradiation of visible light. The non-metal catalyst is used, so that the reaction cost is reduced; the reaction conditions are mild, and the reaction can be completed at room temperature; and the method is simple to operate, short in reaction time, simple in post-treatment, high in product yield and more environment-friendly. The method not only has high academic value, but also has a certain industrialization prospect.
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Paragraph 0045-0046
(2021/07/31)
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- Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water
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We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).
- Hikawa, Hidemasa,Nakayama, Taku,Takahashi, Makiko,Kikkawa, Shoko,Azumaya, Isao
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supporting information
p. 4075 - 4084
(2021/07/26)
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- Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
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A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
- Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
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supporting information
p. 1427 - 1431
(2020/11/02)
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- KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes
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KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.
- Nomula, Vishnuvardhan,Rao, Sadu Nageswara
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supporting information
p. 2602 - 2612
(2021/08/03)
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- Method for preparing 2 -phenyl quinazolinone compound
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The invention relates to a preparation method of 2 -phenyl quinazolinone compounds, in particular to II. To the method, 2 - (benzylamino) benzamide compound (I) is used as a raw material for reaction of the experiment model, a simple substance iodine cata
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Paragraph 0054-0056
(2021/10/30)
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- Complementary Reactivity in Selective Radical Processes: Electrochemistry of Oxadiazolines to Quinazolinones
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Electrochemistry has recently emerged as a sustainable approach for efficiently generating radical intermediates utilizing eco-friendly electric energy. An electrochemical process was developed to transform 1,2,4-oxadiazolines under mild conditions. The electrochemical N-O bond cleavage at a controlled oxidation potential led to the selective synthesis of quinazolinone derivatives that could not be obtained by photocatalytic radical processes, indicating complementary reactivities in radical processes. The electrochemical reaction pathways were fully revealed by density functional theory-based investigations.
- Hwang, Ho Seong,Cho, Eun Jin
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supporting information
p. 5148 - 5152
(2021/07/19)
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- Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones
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Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.
- Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.
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supporting information
p. 8297 - 8302
(2021/03/01)
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- Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage
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This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.
- Xie, Zongbo,Lan, Jin,Yan, Liyuan,Chen, Xuehua,Li, Qian,Meng, Jia,Le, Zhanggao
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p. 2436 - 2441
(2021/04/02)
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- Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α?keto acids with 2-aminobenzamides
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Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α?keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction conditions (room temperature and air atmosphere), and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.
- Tian, Qing,Wei, Yu,Xu, Liang,Zhang, Jinli
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- α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
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A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
- Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
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p. 14866 - 14882
(2021/10/25)
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- Electrochemical Synthesis of Quinazolinones by the Metal-Free and Acceptor-Free Dehydrogenation of 2-Aminobenzamides
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An efficient approach has been developed for the construction of quinazolin-4(3 H)-ones by the selective anodic dehydrogenative oxidation/cyclization of benzylic chlorides and 2-aminobenzamides. The method features acceptor-free and metal-free dehydrogenation of amines to imines; a subsequent intermolecular addition provides the products in moderate to good yields.
- Yao, Yan,Meng, Xiu-Jin,Teng, Qing-Hu,Chen, Yan-Yan
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supporting information
p. 1795 - 1799
(2020/09/07)
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- Ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H)-ones: A convergent synthetic route to bouchardatine and sildenafil
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A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra) in a highly convergent manner. This journal is
- Kim, Hun Young,Kim, Kyeongha,Oh, Kyungsoo
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p. 31101 - 31105
(2020/09/23)
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- Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
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Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
- Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
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supporting information
p. 5435 - 5441
(2020/08/03)
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- Synthetic method of quinazolinone derivatives
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The invention discloses a method for synthesizing quinazolinone derivatives, belonging to the technical field of organic synthesis. According to the preparation method, isatoic anhydride or derivatives thereof, aldehyde compounds and inert amide are used as raw materials and are subjected to one-step synthesis treatment to prepare the quinazolinone derivatives; synthesis steps are simple, raw materials are non-toxic, cheap and easy to obtain, and the synthesis method has the advantages of good functional group compatibility and high atom economy, and has the potential in large-scale one-step preparation of the quinazolinone derivatives.
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Paragraph 0046-0054
(2020/10/14)
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- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
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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.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
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p. 3160 - 3170
(2019/08/07)
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- Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization
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An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.
- Xie, Lijuan,Lu, Cong,Jing, Dong,Ou, Xinrui,Zheng, Ke
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supporting information
p. 3649 - 3653
(2019/06/04)
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- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
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A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
- Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
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p. 9201 - 9209
(2018/07/13)
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- Pd-Catalyzed Regioselective Mono-Arylation: Quinazolinone as the Inherent Directing Group for C(sp2)-H Activation
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The Pd-catalyzed quinazolinone-directed regioselective monoarylation of aromatic rings by C-H bond activation is developed. A broad substrate scope is demonstrated for both quinazolinone as well as diaryliodonium triflates. The use of a base was found to be crucial for this transformation, unlike for the known nitrogen-directed arylations. All of the novel quinazolinones of biological interest were synthesized by using the operationally simple Pd(II)-catalyzed arylation reaction.
- Garad, Dnyaneshwar N.,Viveki, Amol B.,Mhaske, Santosh B.
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p. 6366 - 6372
(2017/06/23)
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- Approach to the Synthesis of 2,3-Disubstituted-3H-quinazolin-4-ones Mediated by Ph3P-I2
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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.
- Phakhodee, Wong,Wangngae, Sirilak,Pattarawarapan, Mookda
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p. 8058 - 8066
(2017/08/14)
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- I2-Catalyzed cross dehydrogenative coupling: Rapid access to benzoxazinones and quinazolinones
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An efficient and applicable I2-catalyzed intramolecular dehydrogenative C-O/C-N coupling reaction via activating the C-H bond adjacent to the N atom has been developed to provide dozens of substituted benzoxazinones (31 examples) and quinazolinones (5 examples) in good to excellent yields (up to 98%). This one-pot methodology has significant advantages, including a metal-free process, broad substrate scope, high atom economy, and simple operation. This strategy goes through an iminium intermediate followed by nucleophilic attack to provide the desired products.
- Chen, Kaili,Gao, Biao,Shang, Yanguo,Du, Jianyao,Gu, Qinlan,Wang, Jinxin
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p. 8770 - 8779
(2017/11/03)
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- Synthesis of Cu-catalysed quinazolinones using a Csp3-H functionalisation/cyclisation strategy
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A series of 2,3-disubstituted-4(3H)-quinazolinones were synthesised via a copper-catalysed Csp3-H functionalisation/cyclisation of 2-amino-N,N-dialkylbenzamides. In comparison to the reported methods this strategy allows an easy access to diversely substituted quinazolinones under mild conditions in air. The reaction also exhibits good functional group tolerance and would be of value to heterocyclic researchers as well as pharmaceutical process chemists. The reaction is proposed to proceed through a double SET type radical mechanism.
- Gholap, Aniket V. A.,Maity, Soham,Schulzke, Carola,Maiti, Debabrata,Kapdi, Anant R.
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p. 7140 - 7146
(2017/09/07)
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- Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant
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A highly efficient, iron nitrate/TEMPO-catalyzed approach for the synthesis of quinazolinones has been achieved via a one-pot, tandem aerobic oxidative cyclization of primary alcohols with 2-aminobenzamides. This practical reaction tolerates a broad scope of substrates and could afford a variety of desirable products in good to excellent yields with air as the terminal green oxidant. Thus, the present synthetic protocol provides an efficient and concise strategy for the synthesis of quinazolinones.
- Hu, Yongke,Chen, Lei,Li, Bindong
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p. 65196 - 65204
(2016/07/21)
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- Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
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A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
- Wang, Zhen-Zhen,Tang, Yu
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p. 1330 - 1336
(2017/02/15)
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- Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions
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The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.
- Kotipalli, Trimurtulu,Kavala, Veerababurao,Janreddy, Donala,Bandi, Vijayalakshmi,Kuo, Chun-Wei,Yao, Ching-Fa
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p. 1182 - 1193
(2016/03/05)
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- Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
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An efficient and practical copper-catalyzed consecutive synthesis of quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones from easily available 2-halobenzamides (or 2-halonicotinamides), aldehydes, and sodium azide has been developed, which gave the corresponding target products in 50-95% yields for 29 examples. This remarkable consecutive process involved sequential copper-catalyzed SNAr, reduction, cyclization, and oxidation. Notably, this work would provide a novel synthetic strategy for bioactive molecules containing quinazolinone class skeletons.
- Li, Ting,Chen, Minglu,Yang, Lei,Xiong, Zhengxin,Wang, Yongwei,Li, Fei,Chen, Dongyin
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p. 868 - 874
(2016/01/20)
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- Development of a New Synthetic Method for Quinazolinones via Aerobic Oxidation in dimethylsulfoxide
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The present invention relates to a method for preparing quinazoline derivatives by aerobic oxidation using oxygen as an oxidizing agent in dimethylsulfoxide (DMSO) solvent wherein metal and base are excluded. The method for preparing quinazoline derivatives according to the present invention does not require any metal catalyst such as palladium or iridium, and thus does not cause toxicity problem of residual metal; and does not require demanding processes such as strong acid, or base conditions, low temperature reactions, or reactions of anhydrous conditions and thus, it is possible to simply and economically prepare quinazoline derivatives by reacting anthranilamide derivatives and an aldehyde source.
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Paragraph 0171-0174; 0219-0222
(2021/03/30)
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- Metal- and Oxidant-Free Synthesis of Quinazolinones from β-Ketoesters with o-Aminobenzamides via Phosphorous Acid-Catalyzed Cyclocondensation and Selective C-C Bond Cleavage
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A general and efficient phosphorous acid-catalyzed cyclocondensation of β-ketoesters with o-aminobenzamides via selective C-C bond cleavage leading to quinazolinones is developed. This reaction proceeds smoothly under metal- and oxidant-free conditions, giving both 2-alkyl- and 2-aryl-substituted quinazolinones in excellent yields. This strategy can also be applied to the synthesis of other N-heterocycles, such as benzimidazoles and benzothiazoles.
- Li, Zhongwen,Dong, Jianyu,Chen, Xiuling,Li, Qiang,Zhou, Yongbo,Yin, Shuang-Feng
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p. 9392 - 9400
(2015/10/12)
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- [Fe(F20TPP)Cl]-catalyzed amination with arylamines and {[Fe(F20TPP)(NAr)](PhI=NAr)}+. Intermediate assessed by high-resolution ESI-MS and DFT calculations
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Amination of C-H bonds catalyzed by transition metal complexes via nitrene/imide insertion is an appealing strategy for C-N bond formation, and the use of iminoiodinanes, or their in situ generated forms from 'PhI-(OAc)2 + primary amides (such as sulfonamides, sulfamates, and carbamates)', as nitrogen sources for the amination reaction has been well documented. In this work, a 'metal catalyst + PhI(OAc)2 + primary arylamines' amination protocol has been developed using [Fe(F20TPP)Cl] (H2F20TPP = meso-tetrakis(pentafluorophenyl)porphyrin) as a catalyst. This catalytic method is applicable for both intra- and intermolecular amination of sp2 and sp3 C-H bonds (> 27 examples), affording the amination products, including natural products such as rutaecarpine, in moderate-to-good yields. ESI-MS analysis and DFT calculations lend support for the involvement of {[Fe(F20TPP)(NC6H4-p-NO2)](PhI=NC6H4-p-NO2)}+. intermediate in the catalysis.
- Liu, Yungen,Chen, Guo-Qiang,Tse, Chun-Wai,Guan, Xianguo,Xu, Zheng-Jiang,Huang, Jie-Sheng,Che, Chi-Ming
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supporting information
p. 100 - 105
(2015/02/19)
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- Cu/Pd-catalyzed C-2-H arylation of quinazolin-4(3H)-ones with (hetero)aryl halides
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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
- Godeau, Julien,Harari, Marine,Laclef, Sylvain,Deau, Emmanuel,Fruit, Corinne,Besson, Thierry
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p. 7705 - 7717
(2015/12/31)
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- Reversible P(III)/P(V) redox: Catalytic aza-Wittig reaction for the synthesis of 4(3H)-quinazolinones and the natural product vasicinone
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The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph 3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81-95% yields and >99% ee).
- Wang, Long,Wang, Ying,Chen, Min,Ding, Ming-Wu
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p. 1098 - 1104
(2014/04/03)
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- Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO
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A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation.
- Kim, Na Yeun,Cheon, Cheol-Hong
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supporting information
p. 2340 - 2344
(2014/05/06)
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- Syntheses of quinazolinones from 2-iodobenzamides and enaminones via copper-catalyzed domino reactions
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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
- Songsichan, Teerawat,Promsuk, Jaturong,Rukachaisirikul, Vatcharin,Kaeobamrung, Juthanat
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p. 4571 - 4575
(2014/06/24)
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- Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
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A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.
- Zhao, Dan,Wang, Teng,Li, Jian-Xin
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supporting information
p. 6471 - 6474
(2014/06/09)
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- Synthesis of quinazolinones from alcohols via laccase-mediated tandem oxidation
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This paper describes the synthesis of quinazolinones via a tandem reaction using the laccase-mediator system under mild conditions. The procedure involved the laccase-catalyzed oxidation of alcohols to the corresponding aldehydes, followed by cyclocondensation with isatoic anhydride and a number of amines to afford 2,3-dihydroquinazolin-4(1H)-ones, which were further oxidized to quinazolinones in useful yields. The use of an enzyme as the catalyst, O 2 as an environmentally friendly oxidant, and a citrate buffer as the green solvent represents a novel and efficient approach for the one-pot synthesis of quinazolinones.
- Heidary, Marjan,Khoobi, Mehdi,Ghasemi, Sabrieh,Habibi, Zohreh,Faramarzi, Mohammad Ali
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p. 1789 - 1794
(2014/06/09)
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- Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency
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An efficient metal-free aerobic oxidative C-N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency, in which all of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles. This journal is the Partner Organisations 2014.
- Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Han, Daoqing,Han, Li-Biao,Yin, Shuang-Feng
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supporting information
p. 3802 - 3807
(2014/06/09)
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- 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
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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
- Guo, Shenghai,Li, Yan,Tao, Li,Zhang, Wenwen,Fan, Xuesen
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p. 59289 - 59296
(2015/02/19)
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- Iron-catalyzed one-pot 2,3-diarylquinazolinone formation from 2-nitrobenzamides and alcohols
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A novel approach for the synthesis of 2,3-diarylquinazolinones using iron as catalyst is described. Various 2-nitro-N-arylbenzamides reacted with benzylic alcohols to selectively give the corresponding products in the absence of external oxidant or reduct
- Wang, Huamin,Cao, Xiangxiang,Xiao, Fuhong,Liu, Saiwen,Deng, Guo-Jun
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supporting information
p. 4900 - 4903
(2013/10/08)
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- One-pot synthesis of quinazolinones from anthranilamides and aldehydes via p -toluenesulfonic acid catalyzed cyclocondensation and phenyliodine diacetate mediated oxidative dehydrogenation
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A variety of 4(3H)-quinazolinones are synthesized conveniently in one pot from 2-aminobenzamides and aldehydes, via cyclization catalyzed by p-toluenesulfonic acid followed by oxidative dehydrogenation mediated by the hypervalent iodine compound phenyliodine diacetate [PhI(OAc)2, PIDA]. Highlights of the described method include the first synthesis of quinazolinones bearing an N-alkoxy substituent, a new application of phenyliodine diacetate as an efficient dehydrogenative oxidant, and mild reaction conditions. Georg Thieme Verlag Stuttgart, New York.
- Cheng, Ran,Guo, Tianjian,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 2998 - 3006
(2013/11/06)
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- Cobalt- and iron-catalyzed redox condensation of o-substituted nitrobenzenes with alkylamines: A step- and redox-economical synthesis of diazaheterocycles
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A wide variety of functionalized 2-aryl benzimidazoles can be prepared by a solvent-free cobalt- or iron-catalyzed redox condensation of 2-nitroanilines and benzylamines. The cascade including benzylamine oxidation, nitro reduction, condensation, and aromatization occurs without any added reducing or oxidizing agent. The method can be extended to other alkylamines as reducing components or 2-nitrobenzamides as oxidizing components when using an iron/sulfur catalyst to afford various diazaheterocycles.
- Nguyen, Thanh Binh,Bescont, Julie Le,Ermolenko, Ludmila,Al-Mourabit, Ali
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supporting information
p. 6218 - 6221
(2014/01/17)
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- Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
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Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis. The Royal Society of Chemistry 2012.
- Fang, Jie,Zhou, Jianguang
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supporting information; experimental part
p. 2389 - 2391
(2012/04/11)
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- Pd-catalyzed benzylic C-H amidation with benzyl alcohols in water: A strategy to construct quinazolinones
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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.
- Hikawa, Hidemasa,Ino, Yukari,Suzuki, Hideharu,Yokoyama, Yuusaku
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experimental part
p. 7046 - 7051
(2012/10/07)
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- KAl(SO4)2·12H2O (Alum) catalyzed one-pot three-component synthesis of 2-alkyl and 2-aryl-4(3H)-quinazolinone under microwave irradiation and solvent free conditions
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Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materials in the presence of KAl(SO4)2·12H 2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3- phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3-phenethylquinazolin- 4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Twenty 2,3-disubstituted-4(3H)-quinazolinones were synthesed by one-pot three-component method with isatoic anhydride, orthoesters and amines as raw materi-als in the presence of KAl(SO4) 2·12H2O (Alum) under microwave irradiation and solvent-free conditions. 6-Bromo-2-propyl-3-p-tolylquinazolin-4(3H)-one (4m), 6-bromo-2-methyl-3-phenethylquinazolin-4(3H)-one (4n) and 6-bromo-2-ethyl-3- phenethylquina-zolin-4(3H)-one (4o) were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Copyright
- Mohammadi, Ali A.,Sadat Hossini
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experimental part
p. 1982 - 1984
(2012/06/04)
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