- Aluminium nitrate-catalyzed one-pot synthesis of 4(3h)-quinazolinones by a three-component coupling of anthranilic acid, amines, and ortho esters
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The one-pot synthesis of quinazolinone derivatives from the reaction of anthranilic acid, amines, and ortho esters in the presence of aluminium nitrate has been carried out. The reaction occurred in a few minutes at room temperature under solvent-free con
- Wang, Min,Song, Zhiguo,Zhang, Tingting
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- Convergent one-pot synthesis of 3-substituted quinazolin-4(3H)-ones under solvent-free conditions
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A convenient method for the synthesis of 3-substituted quinazolin-4(3H)- ones using the convergent reactions of formic acid, a primary amine, and isatoic anhydride under solvent-free conditions and with brief microwave irradiation is described. Copyright Taylor & Francis Group, LLC.
- Rad-Moghadam, Kurosh,Mamghani, Manoochehr,Samavi, Laleh
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- Zirconyl(IV) chloride catalyzed three component one-pot synthesis of quinazolin-4(3H)-ones
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An efficient one-pot method for synthesis of an array of quinazolin-4(3H)-ones from anthranilic acid, triethyl orthoformate, and amines using ZrOCl2 is described. This method offers improvements for the synthesis of quinazolin-4(3H)-ones with r
- Sangshetti, Jaiprakash N.,Kokare, Nagnnath D.,Shinde, Devanand B.
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- Dimerization of substituted 2-aminobenzoic acids under Vilsmeier conditions: A novel route to the synthesis of 4-(3H)-quinazolinones
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Various substituted 2-aminobenzoic acids on treatment with Vilsmeier reagent (DMF/POCl3) at 80-90°C undergo a novel dimerization reaction to yield 2-[3,4-dihydro-4-oxo-3-quinazolinoyl]-N,N-dimethyl benzamides. The interruption of dimerization a
- Majo, Vattoly J.,Perumal, Paramasivan T.
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- Facile synthesis of substituted quinazolin-4-(3H)-ones using low-valence titanium reagent
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A short and facile synthesis of a series of 3-aryl quinazolin-4-(3H)-ones was accomplished in good yields via the intermolecular reductive coupling reaction of N-aryl-2-nitrobenzamide and triethyl orthoformate promoted by TiCl4/Zn.
- Shi, Daqing,Rong, Liangce,Wang, Juxian,Zhuang, Qiya,Wang, Xiangshan,Hu, Hongwen
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- Synthesis of 3-Aryl-4(3H)-quinazolinones from anthranilic acid, ortho esters, and anilines using Ce(CH3SO3)3· 2H2O as catalyst
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3-Aryl-4(3H)-quinazolinones were synthesized efficiently by the three component one-pot cyclocondensation of anthranilic acid, ortho esters, and anilines in the presence of Ce(CH3SO3)3·2H 2O at room temperature under solve
- Wang, Min,Song, Zhi-Guo,Zhang, Ting-Ting
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- SnCl2·2H2O-catalyzed one-pot synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions
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(Chemical Equation Presented) A simple, efficient, and green procedure for the one-pot synthesis of 4(3H)-quinazolinones by three components condensation of anthranilic acid, ortho esters, and amines in the presence of SnCl 2·2H2O ha
- Wang, Min,Song, Zhiguo,Zhang, Tingting
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- Synthesis of Quinazolinones, Imidazo[1,2-c]quinazolines and Imidazo[4,5-c]quinolines through Tandem Reductive Amination of Aryl Halides and Oxidative Amination of C(sp3)–H Bonds
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A tandem multicomponent approach has been described for the synthesis of quinazolinones, imidazo[1,2-c]quinazolines and imidazo[4,5-c]quinolines. The reaction involves a copper-catalyzed reductive amination through azidation followed by reduction and oxidative amination of C(sp3)–H bonds of N,N-dimethylacetamide in the presence of TBHP (tert-butylhydroperoxide) as oxidant. The method uses the easily available sodium azide as a nitrogen source and DMA (N,N-dimethylacetamide) as a one-carbon source for the synthesis of these N-fused heterocycles in good to excellent yields. The reaction can also be used for gram-scale synthesis.
- Nandwana, Nitesh Kumar,Dhiman, Shiv,Saini, Hitesh Kumar,Kumar, Indresh,Kumar, Anil
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- A convenient synthesis of substituted quinazolin-4(3H)-ones under microwave and solvent-free conditions
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A clean and facile synthesis of the title compounds is achieved from cyclocondensation of 2-aminobenzamides with orthoesters catalyzed by SiO 2/H2SO4 in dry and microwave conditions.
- Montazeri, Nasser,Rad-Moghadam, Kurosh
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- Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones
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Photoinduced transformations of 2-styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2-(hydroxyaryl)ethenyl derivatives by changin
- Ovchinnikova,Kim,Matochkina,Kodess,Barykin,E?tsov,Nosova,Rusinov,Charushin
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- Synthesis method of 4-3(H)quinazolinone and its derivatives
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The present invention provides a method for synthesizing 4- (3H) quinazolinone and derivatives thereof (formula III), the method takes imidazole hydrochloride as the catalyst, in the absence of other catalysts or additives, by the one-pot method of synthesis of 2,3-di substituted quinazolinone and its derivatives by a pot method of 2,3-di substituted quinazolinone and its derivatives. The synthesis method of the present invention has good functional group tolerance, capable of synthesizing 4-(3H) quinazolinone and its derivatives for research in drugs or other fields. The synthesis method of the present invention does not use dichloromethane, nor does it use a corrosive concentrated hydrochloric acid and metal catalyst, while not requiring harsh reaction conditions, no gas protection, no autoclave, the reaction time is short, has a certain value in industrial production.
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Paragraph 0061-0064; 0067-0068; 0072
(2022/03/31)
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- Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones
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A simple copper-catalyzed assembly to formulate quinazolinone and indazolone derivatives in a single protocol manner is reported. These transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construct
- Govindan, Karthick,Duraisamy, Tamilselvan,Jayaram, Alageswaran,Senadi, Gopal Chandru,Lin, Wei-Yu
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supporting information
p. 1115 - 1124
(2021/12/02)
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- N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
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N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
- Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
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p. 16848 - 16857
(2021/12/06)
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- Tunable Electrosynthesis of Anthranilic Acid Derivatives via a C-C Bond Cleavage of Isatins
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A facile and direct electrocatalytic C-C bond cleavage/functionalization reaction of isatins was developed. With isatins as the amino-attached C1 sources, a variety of aminobenzoates, and aminobenzamides were synthesized in moderate to good yields under mild conditions.
- Qian, Peng,Liu, Jiaojiao,Zhang, Yan,Wang, Zhiyong
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p. 16008 - 16015
(2021/07/31)
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- Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
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The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
- Kudale, Vishal Suresh,Wang, Jeh-Jeng
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supporting information
p. 3506 - 3511
(2020/06/25)
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- Transition-metal and oxidant-free approach for the synthesis of diverse N-heterocycles by TMSCl activation of isocyanides
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A highly efficient TMSCl-mediated addition of N-nucleophiles to isocyanides has been achieved. This transition-metal and oxidant-free strategy has been applied to the construction of various N-heterocyles such as quinazolinone, benzimidazole and benzothiazole derivatives by the use of distinct amino-based binucleophiles. The notable feature of this protocol includes its mild reaction condition, broad functional group tolerance and excellent yield. This journal is
- Chen, Fen-Er,Dong, Lin,Li, Hongyan,Liu, Jinxin,Luo, Liangliang,Xiao, You-Cai,Zhou, Yuan
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p. 29257 - 29262
(2020/10/02)
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- Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
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N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
- Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
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supporting information
p. 5726 - 5733
(2020/08/21)
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- Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones
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A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.
- He, Junhui,Dong, Jianyu,Su, Lebin,Wu, Shaofeng,Liu, Lixin,Yin, Shuang-Feng,Zhou, Yongbo
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supporting information
p. 2522 - 2526
(2020/04/09)
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- New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid
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A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.
- Niu, Bin,Li, Shaoqing,Cui, Chang,Yan, Yizhe,Tang, Lin,Wang, Jianyong
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supporting information
p. 7800 - 7803
(2019/11/28)
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- Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions
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The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.
- Vaidya, Gargi Nikhil,Khan, Arif,Verma, Hansa,Kumar, Sanjeev,Kumar, Dinesh
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p. 3004 - 3010
(2019/03/07)
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- Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol
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In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.
- Komar, Mario,Konjarevi?, Anastazija,Molnar, Maja
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- Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles
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A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF2COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF
- Yan, Yizhe,Cui, Chang,Wang, Jianyong,Li, Shaoqing,Tang, Lin,Liu, Yanqi
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supporting information
p. 8071 - 8074
(2019/09/19)
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- Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon
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Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield.
- Lee, Seohoo,Sim, Jaeuk,Jo, Hyeju,Viji, Mayavan,Srinu, Lanka,Lee, Kiho,Lee, Heesoon,Manjunatha, Vishwanath,Jung, Jae-Kyung
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supporting information
p. 8067 - 8070
(2019/09/19)
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- Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
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Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
- Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
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p. 979 - 985
(2019/03/12)
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- TBHP as Methyl Source under Metal-Free Aerobic Conditions To Synthesize Quinazolin-4(3H)-ones and Quinazolines by Oxidative Amination of C(sp3)–H Bond
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tert-Butyl hydroperoxide (TBHP) served as the methyl source under metal-free aerobic conditions in the oxidative amination of the C(sp3)–H bond to synthesize quinazolin-4(3H)-ones and quinazolines from 2-aminobenzamides and 2-carbonyl-substituted anilines, respectively.
- Mukhopadhyay, Sushobhan,Barak, Dinesh S.,Batra, Sanjay
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p. 2784 - 2794
(2018/06/04)
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- Furan-2-carbaldehydes as C1 building blocks for the synthesis of quinazolin-4(3: H)-ones via ligand-free photocatalytic C-C bond cleavage
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Furan-2-carbaldehydes, as biomass-derived chemicals, are used as efficient green C1 building blocks to synthesize bioactive quinazolin-4(3H)-ones by ligand-free photocatalytic C-C bond cleavage. Notably, protection of hydroxyl, carboxyl, amide, or secondary amino groups is not required. Mechanistic studies suggest that conjugated N,O-tridentate copper complexes act as novel photoinitiators under visible light.
- Yu, Wenjia,Zhang, Xianwei,Qin, Bingjie,Wang, Qiyang,Ren, Xuhong,He, Xinhua
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supporting information
p. 2449 - 2454
(2018/06/11)
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- One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
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A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).
- Cao, Liu,Huo, Hengrui,Zeng, Haipeng,Yu, Yu,Lu, Dengfu,Gong, Yuefa
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supporting information
p. 4764 - 4773
(2018/11/10)
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- A facile synthesis of quinazolinone derivatives through Vilsmeier intermediate
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The reaction of ethyl 2-aminobenzoate with different substituted amide compounds led to cyclization through Vilsmeier intermediate in dry dichloromethane and ambient temperature, affording the 4(3H)-quinazolinone derivatives with higher yields. The struct
- Mohammed, Shireen,Khalid, Maher
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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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- Fragment Discovery for the Design of Nitrogen Heterocycles as Mycobacterium tuberculosis Dihydrofolate Reductase Inhibitors
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Fragment-based drug design was used to identify Mycobacterium tuberculosis (Mtb) dihydrofolate reductase (DHFR) inhibitors. Screening of ligands against the Mtb DHFR enzyme resulted in the identification of multiple fragment hits with IC50 values in the range of 38–90 μM versus Mtb DHFR and minimum inhibitory concentration (MIC) values in the range of 31.5–125 μg/mL. These fragment scaffolds would be useful for anti-tubercular drug design.
- Shelke, Rupesh U.,Degani, Mariam S.,Raju, Archana,Ray, Mukti Kanta,Rajan, Mysore G. R.
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p. 602 - 613
(2016/08/28)
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- Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives
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We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.
- Xu, Wei,Zhu, Xiao-Rui,Qian, Peng-Cheng,Zhang, Xing-Guo,Deng, Chen-Liang
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supporting information
p. 2851 - 2857
(2016/12/16)
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- Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon
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A novel and efficient oxidative annulation of 2-aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N-substituted 1,2,3-benzotriazine-4(3H)-ones in moderate to excellent yields under transition metal-free conditions. T
- Yan, Yizhe,Niu, Bin,Xu, Kun,Yu, Jianhua,Zhi, Huanhuan,Liu, Yanqi
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supporting information
p. 212 - 217
(2016/02/14)
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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; 0207-0210
(2021/03/30)
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- Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs
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Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.
- Kumar, Dinesh,Jadhavar, Pradeep S.,Nautiyal, Manesh,Sharma, Himanshu,Meena, Prahlad K.,Adane, Legesse,Pancholia, Sahaj,Chakraborti, Asit K.
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p. 30819 - 30825
(2015/04/22)
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- Pd/C as an efficient heterogeneous catalyst for carbonylative four-component synthesis of 4(3H)-quinazolinones
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Quinazolinones are of interest in the fields of pharmaceuticals and medicinal chemistry. The application of palladium on activated charcoal (Pd/C) as a heterogeneous catalyst was investigated for the carbonylation of 2-iodoanilines with trimethyl orthofor
- Natte, Kishore,Neumann, Helfried,Wu, Xiao-Feng
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p. 4474 - 4480
(2015/09/01)
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- I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones
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An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.
- Yan, Yizhe,Xu, Ying,Niu, Bin,Xie, Huifang,Liu, Yanqi
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p. 5581 - 5587
(2015/06/16)
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- Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
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A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
- Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
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p. 4736 - 4742
(2015/05/13)
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- Diversified facile synthesis of benzimidazoles, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones via palladium-catalyzed transfer hydrogenation/condensation cascade of nitro arenes under microwave irradiation
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A highly efficient diversified methodology for preparation of benzimidazole, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones is established using a palladium-catalyzed transfer hydrogenation (CTH)/condensation cascade of o-nitroaniline and o-nitrobenzamides in a triethylamine-formic acid azeotropic mixture (2:5) under microwave irradiation.
- Zhu, Kaicheng,Hao, Jian-Hong,Zhang, Cheng-Pan,Zhang, Jiajun,Feng, Yiqing,Qin, Hua-Li
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p. 11132 - 11135
(2015/03/05)
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- Method For Preparing Nitrogen Compounds
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The present invention relates to a method for preparing nitrogen compounds using carbon dioxide, and to the use of the method in the production of vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers. The invention also relates to a method for producing vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, pesticides, herbicides, antifungal agents and fertilisers, which includes a step of preparing nitrogen compounds using the method of the invention. The invention further relates to a method for preparing labelled nitrogen compounds using carbon dioxide and to the uses thereof.
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Paragraph 0195; 0196
(2015/06/03)
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- Highly efficient four-component synthesis of 4(3H)-quinazolinones: Palladium-catalyzed carbonylative coupling reactions
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Given the importance of quinazolinones and carbonylative transformations, a palladium-catalyzed fourcomponent carbonylative coupling system for the synthesis of diverse 4(3H)-quinazolinone in a concise and convergent fashion has been developed. Starting from 2-bromoanilines (1 mmol), trimethyl orthoformate (2 mmol), and amines (1.1 mmol), under 10 bar of CO, the desired products were isolated in good yields in the presence of Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%) in 1,4-dioxane (2 mL) at 1008C, using N,Ndiisopropylethylamine (2 mmol) as the base. Notably, the process tolerates the presence of various reactive functional groups and is very selective for quinazolinones, and was used in the synthesis of the precursor to the bioactive dihydrorutaempine.
- He, Lin,Li, Haoquan,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
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p. 1420 - 1424
(2014/03/21)
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- A convenient palladium-catalyzed carbonylative synthesis of 4(3H)-quinazolinones from 2-bromoformanilides and organo nitros with Mo(CO) 6 as a multiple promoter
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A novel and convenient procedure for the synthesis of quinazolinones has been developed. Using 2-bromoformanilides and organo nitros as substrates and Mo(CO)6 as a multiple promoter, the desired products were isolated in moderate to excellent yields in the presence of a palladium catalyst. Here, Mo(CO)6 was not only a CO source, but also a nitro compound reducing reagent and a cyclization promoter. This journal is the Partner Organisations 2014.
- He, Lin,Sharif, Muhammad,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 3763 - 3767
(2014/08/05)
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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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- Ammonium chloride-catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions
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Ammonium chloride, which is a very inexpensive and readily available reagent, can efficiently catalyze three-component, one-pot condensation reactions of 2-amino-benzoic acid esters, ortho esters, and aromatic amines to afford the corresponding 4(3H)-quinazolinones in good to excellent yields under solvent-free conditions.
- Huang, Guoli,Liu, Bo,Teng, Mingyu,Chen, Yegao
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supporting information
p. 1786 - 1794
(2014/06/09)
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- Vilsmeier Reagent: An efficient reagent for the transformation of 2-aminobenzamides into quinazolin-4(3 h)-one derivatives
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Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products.
- Farzipour, Soghra,Saeedi, Mina,Mahdavi, Mohammad,Yavari, Hossein,Mirzahekmati, Mohammadreza,Ghaemi, Nasser,Foroumadi, Alireza,Shafiee, Abbas
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p. 481 - 487
(2014/01/23)
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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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- Glyoxylic acid in the reaction of isatoic anhydride with amines: A rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones leading to rutaecarpine and evodiamine
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A dual reactant/catalyst role of glyoxylic acid in the reaction of isatoic anhydride with various amines afforded a novel, robust and rapid synthesis of 3-(un)substituted quinazolin-4(3H)-ones. This metal catalyst-free reaction proceeds via an unusual and unexpected cleavage of C-C bond. A shorter and common route to two alkaloids, that is, rutaecarpine and evodiamine is also accomplished.
- Rao, K. Raghavendra,Raghunadh, Akula,Mekala, Ramamohan,Meruva, Suresh Babu,Pratap,Krishna,Kalita, Dipak,Laxminarayana, Eppakayala,Prasad, Bagineni,Pal, Manojit
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supporting information
p. 6004 - 6006
(2014/12/12)
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- Green synthesis of quinazolinone derivatives catalyzed by iodine in ionic liquid
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A series of quinazolinone derivatives were synthesized by the reaction of 2-aminobenzamides and triethyl orthoformate or triphosgene in ionic liquid of [BMIm]BF4 at 80 °C catalyzed by iodine in good yields. Compared to other methods, this new procedure has the advantages of mild reaction conditions, good yields, operational simplicity, and environmentally friendly procedure. Copyright Taylor & Francis Group, LLC.
- Wang, Shu-Liang,Yang, Ke,Yao, Chang-Sheng,Wang, Xiang-Shan.
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experimental part
p. 341 - 349
(2011/11/12)
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- Pentafluorophenylammonium triflate: An efficient, practical and environmental friendly catalyst for synthesis of quinazolin-4(3H)-ones
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An efficient, solvent-free, clean and facile synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from cyclocondensation of 2-aminobenzamides with orthoesters catalyzed by pentafluorophenylammonium triflate under microwave irradiation conditions is descri
- Montazeri, Naser,Pourshamsian, Khalil,Rahgol, Mehdi,Bayazi, Masoud
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experimental part
p. 5361 - 5364
(2012/10/18)
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- Synthesis of 2,3-disubstituted-4(3H)-quinazolinones using hy-zeolite as reusable catalyst under microwave irradiation
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A new heterogeneous catalytic method to synthesize to various 4(3H)-quinazolinone derevatives, using an inexpensive and eco-friendly attractive solid catalyst, zeolite, under solvent-free and microwave irradiation conditions is described. The catalyst activity results suggest that the methodology adopted offers several advantages such as mild reaction conditions, low loading of catalyst, good yields, short reaction time and operational simplicity.
- Montazeri, Naser,Pourshamsian, Khalil,Fomani, Arsalan,Kalantarian, Seyd Jafar
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experimental part
p. 2805 - 2807
(2012/08/28)
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- An efficient, greener, and solvent-free one-pot multicomponent synthesis of 3-substituted quinazolin-4(3H)ones and thienopyrimidin-4(3H)ones
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Herein, we report an efficient, greener, and solvent-free novel method for the synthesis of 3-substituted quinazolin-4(3H)ones and thienopyrimidin-4(3H) ones in a one-pot sequence using methyl anthranilate or 2-aminothiophene-3- carboxylate with N,N′-dimethyl formamide dimethyl acetal and various anilines. The driving force for this reaction is the removal of N,N′-dimethylamine by various anilines resulting in 3-substituted quinazolin-4(3H)ones and thienopyrimidin-4(3H)ones.
- Jalani, Hitesh B.,Pandya, Amit N.,Pandya, Dhaivat H.,Sharma, Jayesh A.,Sudarsanam,Vasu, Kamala K.
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p. 4062 - 4064
(2012/08/28)
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- Synthesis of 3-substituted and 2,3-disubstituted quinazolinones via Cu-catalyzed aryl amidation
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CuI/4-hydroxy-l-proline catalyzed coupling of N-substituted o-bromobenzamides with formamide takes place at 80 °C, affording 3-substituted quinazolinones directly. Under these conditions other amides that were tested only provided simple coupling products, which can be converted into 2,3-disubstituted quinazolinones via HMDS/ZnCl2 mediated condensative cyclization.
- Xu, Lanting,Jiang, Yongwen,Ma, Dawei
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supporting information; experimental part
p. 1150 - 1153
(2012/03/27)
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- Synthesis of 4-(3H)-quinazolinones by microwave assisted tandem reaction and evaluation of their antibacterial and antifungal activities
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A one-pot synthesis of quinazolinone derivatives from the reaction of anthranilic acid and primary aromatic amines with Vilsmeier reagent (DMF/POCl3) has been carried out. The reaction occurred in a few minutes under microwave irradiation provi
- Priya, M. Gnana Ruba,Zulykama,Girija,Murugesh,Perumal
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experimental part
p. 98 - 102
(2011/04/22)
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- Dabco as a novel and efficient catalyst for the synthesis of 4(3H)-Quinazolinone derivatives
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4(3H)-Quinazolinones were synthesized in high to excellent yields through the one-pot condensation of anthranilic acid, trimethyl orthoformate and primary amines in the presence of DABCO under solvent free conditions.
- Heravi, Majid M.,Javanmardi, Najme,Oskooie, Hossein A.,Baghernejad, Bita
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scheme or table
p. 305 - 308
(2012/04/17)
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- Building heterocyclic systems with RC(OR)2+ carbocations in recyclable bronsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH 3][NO3] and [PMIM(SO3H)][OTf]
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1-Aryl/alkyl-1H-1,2,3,4-tetrazoles can conveniently be synthesized in one-pot reactions from the corresponding amines by reaction with TMSN 3 and CH(OEt)3 using the readily available, recyclable, Bronsted acidic ionic liquids [EtNH3][NO3] IL-1 and [PMIM(SO3H)][OTf] IL-2 under mild conditions in high yields. Based on comparative reactions, whereas both ILs are excellent promoters, reactions are completed with shorter reaction times and in higher yields with IL-2. Among 24 examples provided, identical products were obtained via the two ILs, except in the case of 2-aminobenzoic acid where tetrazole was formed with IL-2 and 2-ethylquinazolin-4(3H)-one was formed with IL-1. By leaving out TMS-N 3 from the reaction, the in-situ formed CH(OEt)2 + and EtC(OEt)2+ (via their corresponding orthoesters) react under sonication with o-phenylenediamine bearing various substituents, o-aminothiophenol and o-aminophenol to form a wide array of benzazoles (benzimidazole, benzothiazole and benzoxazole) and quinazolin-4(3H)-one in high yields (18 examples). The two ILs reacted differently in reaction with 2-aminobenzamide, whereas quinazolin-4(3H)one was formed with IL-2/CH(OEt)3, the "unexpected" N-ethylquinazolin-4(3H)one was isolated with IL-1/CH(OEt)3. The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt)3. Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and re-use of the ILs.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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scheme or table
p. 2827 - 2835
(2011/06/23)
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