- Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones fromo-nitrobenzamide and alcohols
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Palladium-catalyzed 2-substituted quinazolin-4(3H)-one formation from readily availableo-nitrobenzamides and alcohols using hydrogen transfer is described. Various quinazolin-4(3H)-ones were obtained in good to high yields. The cascade reaction including
- Wang, Ke,Chen, Hao,Dai, Xinyan,Huang, Xupeng,Feng, Zhiqiang
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p. 13119 - 13123
(2021/04/22)
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- Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst
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Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.
- Thorve, Pradip Ramdas,Maji, Biplab
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p. 1116 - 1124
(2021/02/26)
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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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- 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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- Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
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Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.
- Liu, Xuexin,Chen, Jian,Yang, Chunyan,Wu, Zhouping,Li, Zhiyang,Shi, Yuesen,Huang, Tianle,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 6831 - 6835
(2021/09/08)
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- Zinc Stabilized Azo-anion Radical in Dehydrogenative Synthesis of N-Heterocycles. An Exclusively Ligand Centered Redox Controlled Approach
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Herein we report an exclusively ligand-centered redox controlled approach for the dehydrogenation of a variety of N-heterocycles using a Zn(II)-stabilized azo-anion radical complex as the catalyst. A simple, easy-to-prepare, and bench-stable Zn(II)-complex (1b) featuring the tridentate arylazo pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline, in the presence of zinc-dust, undergoes reduction to form the azo-anion radical species [1b]- which efficiently dehydrogenates various saturated N-heterocycles such as 1,2,3,4-tetrahydro-2-methylquinoline, 1,2,3,4-tetrahydro-isoquinoline, indoline, 2-phenyl-2,3-dihydro-1H-benzoimidazole, 2,3-dihydro-2-phenylquinazolin-4(1H)-one, and 1,2,3,4-tetrahydro-2-phenylquinazolines, among others, under air. The catalyst has further been found to be compatible with the cascade synthesis of these N-heterocycles via dehydrogenative coupling of alcohols with other suitable coupling partners under air. Mechanistic investigation reveals that the dehydrogenation reactions proceed via a one-electron hydrogen atom transfer (HAT) pathway where the zinc-stabilized azo-anion radical ligand abstracts the hydrogen atom from the organic substrate(s), and the whole catalytic cycle proceeds via the exclusive involvement of the ligand-centered redox events where the zinc acts only as the template.
- Das, Siuli,Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Das, Abhishek,Paul, Nanda D.
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p. 7498 - 7512
(2021/06/30)
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- Iron catalyzed metal-ligand cooperative approaches towards sustainable synthesis of quinolines and quinazolin-4(3H)-ones
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Herein we report simple, efficient, and economically affordable metal-ligand cooperative strategies for synthesizing quinolines and quinazolin-4(3H)-ones via dehydrogenative functionalization of alcohols. Various polysubstituted quinolines and quinazolin-4(3H)-ones were prepared in good yields via dehydrogenative coupling of readily available alcohols with ketones and 2-aminobenzamides, respectively under air using a well-defined Fe(II)-catalyst, ([FeL1Cl2] (1)) bearing a redox-active azo-aromatic pincer 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline) (L1). Control experiments and mechanistic investigation disclose that the one-electron reduced mono-anionic species [1]? bearing an iron-stabilized azo-anion radical ligand catalyzes these reactions. Both iron and the redox-active arylazo ligand participate synergistically during the different steps of these catalytic reactions.
- Mondal, Rakesh,Chakraborty, Gargi,Guin, Amit Kumar,Pal, Subhasree,Paul, Nanda D.
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- Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones
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In this work, ruthenium(II)-catalyzed C?C/C?N annulation of 2-arylquinazolinones with vinylene carbonate is reported to synthesize fused quinazolinones. This catalytic system tolerates a wide range of substrates with excellent functional-group compatibility. In this transformation, the vinylene carbonate acts as an ethynol surrogate without any external oxidant involved. Furthermore, preliminary mechanistic studies were conducted, and a plausible catalytic cycle was also proposed.
- Wang, Zhao-Hui,Wang, He,Wang, Hua,Li, Lei,Zhou, Ming-Dong
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supporting information
p. 995 - 999
(2021/03/03)
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- Method for synthesizing 2 -phenylquinazolone compound by taking styrene compound as raw material
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The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound. The method comprises the steps of adopting a styrene compound and 2-aminobenzamide as reaction raw materials; underthe combined action of a palladium catalyst, a ligand and oxygen, reacting to obtain the 2-phenyl quinazolinone compound, wherein the reaction temperature is 80 DEG C to 110 DEG C, a reaction formulais as shown in the below figure, and R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitro or methoxyl. The method provided by the invention has the beneficial effects that the raw material styrene compound is cheap and easy to get, so that the method is more economical; a preparation method is simple and convenient to operate, and the obtained product is easy to post-process, so that the method is suitable for large-scale industrial production; no high temperature and high pressure is needed, and a reaction condition is mild; the method is short in reaction time, high efficient to react, high in yield, and higher in reaction efficiency after reaction amplification.
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Paragraph 0097-0106
(2021/03/03)
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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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- Imidazolium chloride as an additive for synthesis of 4(3H)-quinazolinones using anthranilamides and DMF derivatives
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Imidazolium chloride as an environmentally benign additive efficiently facilitates construction of 4(3H)-quinazolinones using anthranilamides and DMF derivatives. A series of 4(3H)-quinazolinones were prepared in moderate to excellent yields without conventional oxidants, metal catalysts and corrosive acids or other additives.
- Dai, Zeshu,Li, Dan,Li, Zhiyao,Liu, Heng,Luo, Wen,Shang, Suqin,Tian, Qingqiang,Wang, Shuqi,Wang, Xuetong,Wang, Yin,Wu, Huili,Xiao, Xin,Yuan, Jianyong,Zhou, Shangjun
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- Palladium-catalyzed oxidative homocoupling of 2-arylquinazolinones
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Pd-catalyzed oxidative homocoupling of 2-arylquinazolinones was successfully developed for the direct construction of biaryls via C[sbnd]H bond activation. New well-defined structure that possessed two quinazolinone units was obtained with high efficiency
- Feng, Yadong,Wu, Zhengping,Chen, Ting,Fu, Qi,You, Qihua,Shen, Jinhai,Cui, Xiuling
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supporting information
p. 3263 - 3266
(2020/05/06)
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- Site-Selective C–H Amidation of 2-Aryl Quinazolinones Using Nitrene Surrogates
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The site-selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)-catalyzed C–H amidation of 2-aryl quinazolin-4(3H)-ones with a range of nitrene surrogates including dioxazolones, organic azides, and N-methoxyamides. Complete site-selectivity and functional group tolerance are observed. Notably, the large-scale reaction and late-stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
- Kim, Saegun,Jeoung, Daeun,Kim, Kunyoung,Lee, Seok Beom,Lee, Suk Hun,Park, Min Seo,Ghosh, Prithwish,Mishra, Neeraj Kumar,Hong, Suckchang,Kim, In Su
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supporting information
p. 7134 - 7143
(2020/10/02)
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- Rhodium-catalyzed [4+1] annulation of sulfoxonium ylides: Sequential ortho-C[sbnd]H functionalization/carbonyl α-amination toward polycyclic quinazolinones
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A rhodium-catalyzed [4+1] annulation between 2-aryl quinazolin-4(3H)-ones and sulfoxonium ylides was developed, leading to 12-aroyl isoindolo[1,2-b]quinazolin-10(12H)-ones in moderate to good yields. This reaction proceeds with sequential ortho-C[sbnd]H functionalization of 2-aryl quinazolin-4(3H)-ones and an intramolecular rhodium-catalyzed α-amination of carbonyl to furnish the cyclization. This procedure was applied to access some 13-aroyl luotonin A derivatives whereby the direct construction of ring c.
- Wang, Chang,Qian, Peng-Cheng,Chen, Fan,Cheng, Jiang
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supporting information
(2020/10/05)
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- Cobalt complexes of redox noninnocent azo-aromatic pincers. Isolation, characterization, and application as catalysts for the synthesis of quinazolin-4(3: H)-ones
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Herein we report the synthesis, characterization and catalytic application of three new cobalt(ii)-complexes of redox noninnocent arylazo ligands, 2-(phenylazo)-1,10-phenanthroline (L1a), 2-(4-chlorophenylazo)-1,10-phenanthroline (L1b) and 2,9-bis(phenyldiazo)-1,10-phenanthroline (L2) respectively. The reaction of L1a with CoIICl2·6H2O produced a μ-dichloro bridged binuclear cobalt(ii)-complex [CoII2(L1a)2Cl2] (1a) while the same reaction when carried out with 2-(4-chlorophenyl)azo-1,10-phenanthroline (L1b) and 2,9-bis(phenyldiazo)-1,10-phenanthroline (L2) ligands produced two new mononuclear five-coordinate cobalt(ii)-complexes 1b and 2 respectively. In complex 1a and 1b, the ligands L1a and L1b are coordinated to the cobalt(ii)-center in a tridentate mode utilizing all of its nitrogen donor sites while in complex 2 one of the azo-donor sites of the ligand L2 remain pendant. All these complexes were characterized using available spectroscopic techniques and DFT studies. We further explored the potential of these complexes as catalysts for the synthesis of pharmaceutically important organic compounds via the functionalization of alcohols. A variety of substituted quinazolin-4(3H)-ones were synthesized under aerobic conditions via the coupling of alcohols and 2-aminobenzamide using 1b as the catalyst. Mechanistic investigations revealed that both cobalt and the arylazo scaffold act synergistically during catalysis. This journal is
- Das, Siuli,Mandal, Sutanuva,Mondal, Rakesh,Paul, Nanda D.,Sinha, Suman
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supporting information
p. 8448 - 8459
(2020/07/10)
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- Electron-Withdrawing Substituted Quinazoline Push-Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second-Order Nonlinear Optical Properties
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A series of chromophores bearing 4-cyanoquinazoline, 2-(4-cyanophenyl)quinazoline or 2-(4-trifluorophenyl)quinazoline electron–acceptor (A) and 5-(4-aminophenyl)thiophen-2-yl or 4-aminophenyl electron-donor (D) units has been designed. The influence of the electron-withdrawing substituent on the pyrimidine core as well as the nature of the amino electron donating group has been studied by cyclic voltammetry, UV/Vis and emission spectroscopy. Whereas 2-(4-cyanophenyl)quinazoline and 2-(4-trifluorophenyl)quinazoline derivatives are highly luminescent in chloroform solution, 4-cyanoquinazolines are poorly emissive. Interestingly all compounds are luminescent in the solid state with the emission ranging from blue to red. The second order nonlinear optical properties were studied using electric field induced second harmonic generation (EFISH) method. Quantum-chemical calculations corroborate the aforementioned experimental results.
- Achelle, Sylvain,Barsella, Alberto,Bure?, Filip,Charushin, Valery N.,Le Poul, Pascal,Lipunova, Galina N.,Moshkina, Tatiana N.,Nosova, Emiliya V.,Pytela, Old?ich,Robin-Le Guen, Fran?oise
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- Polystyrene-Supported Palladium (Pd?PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones
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An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd?PS) nanoparticles (NPs) catalyzed con
- Ram, Shankar,Shaifali,Chauhan, Arvind Singh,Sheetal,Sharma, Ajay Kumar,Das, Pralay
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supporting information
p. 14506 - 14511
(2019/11/21)
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- Discovery of Quinazolin-4(3 H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation
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NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C-C triple/double bond and the release of formaldehyde. The reaction relies on the C-N bond formation along with the C-C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.
- Abdullaha, Mohd,Mohammed, Shabber,Ali, Mehboob,Kumar, Ajay,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 5129 - 5140
(2019/04/16)
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- Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles
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A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.
- Wang, Qi,Lv, Miao,Liu, Jianping,Li, Yang,Xu, Qing,Zhang, Xu,Cao, Hongen
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p. 3043 - 3048
(2019/03/17)
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- A quinazolinone of heterocyclic compound synthetic method
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The invention discloses a quinazolinone of heterocyclic compound synthetic method. In under the action of the water-soluble alkali using air as the oxidizing agent, and ortho-amino alcohol oxidation fragrant nitrile compound - cyclized - oxidation of high efficiency series reaction one-step preparation quinazolinone of heterocyclic compound synthetic method. This method does not need the use of expensive transition metal catalyst and ligand, but the use of water-soluble alkali as promoter, the alkali can be removed by water washing mode is convenient, so product transition metal-free residue, is suitable as a pharmaceutical preparation of the precursor, the method condition is simple, easy to operate, low requirement for the device, and can utilizes air as economic security green oxidizing agent, water-soluble alkali as promoter, the only by-product is water, atom economical high, has a certain research and industrial application prospect.
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Paragraph 0067-0070
(2019/07/01)
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- Method for synthesizing quinazolinone derivative
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The invention discloses a method for synthesizing a quinazolinone derivative. According to the method for synthesizing the quinazolinone derivative,anthranilonitrile compounds and primary alcohols areused as raw materials, 2,2,6,6-tetramethylpiperidine ox
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Paragraph 0043-0045
(2019/11/04)
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- Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C-H Bond Activation
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The directed C-H alkynylation of 2-(hetero)arylquinazolin-4-ones has been explored with the ethynylbenziodoxolone reagent TIPS-EBX employing an Ir(III) catalyst. Complementary conditions for either monoalkynylation or dialkynylation have been developed. Also demonstrated is the broad scope of this reaction and the compatibility of various functional groups such as ?F, ?Cl, ?Br, ?CF3, ?OMe, ?NO2, and alkyl, etc.
- Rohokale, Rajendra S.,Kalshetti, Rupali G.,Ramana, Chepuri V.
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supporting information
p. 2951 - 2961
(2019/02/26)
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- Synergistic catalysis on Fe-N: X sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
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In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe-Fe3C nanoparticles and Fe-Nx sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H2O2 as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe-Nx sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles.
- Ma, Zhiming,Song, Tao,Yuan, Youzhu,Yang, Yong
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p. 10283 - 10289
(2019/11/20)
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- Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
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Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4(3H)-ones using mesityl(2,2,2-trifluoroethyl)iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C-H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4(3H)-one family associated with nonradiative decay is presented.
- Maiti, Saikat,Kim, Jaeshin,Park, Jae-Heon,Nam, Dongsik,Lee, Jae Bin,Kim, Ye-Jin,Kee, Jung-Min,Seo, Jeong Kon,Myung, Kyungjae,Rohde, Jan-Uwe,Choe, Wonyoung,Kwon, Oh-Hoon,Hong, Sung You
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supporting information
p. 6737 - 6751
(2019/06/04)
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- Synthesis, Crystal Structure, and Agricultural Antimicrobial Evaluation of Novel Quinazoline Thioether Derivatives Incorporating the 1,2,4-Triazolo[4,3- a]pyridine Moiety
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A total of 22 quinazoline thioether derivatives incorporating a 1,2,4-triazolo[4,3-a]pyridine moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture. Among these compounds, the chemical structure of compound 6l was further confirmed via single-crystal X-ray diffraction analysis. The bioassay results revealed that some of the compounds possessed noticeable in vitro antibacterial activities against the tested phytopathogenic bacteria. For example, compounds 6b and 6g had EC50 values as low as 10.0 and 24.7 μg/mL against Xanthomonas axonopodis pv. citri (Xac), respectively, which were significantly better than that of the commercial agrobactericide bismerthiazol (56.9 μg/mL). Particularly, compound 6b was also found to be capable of suppressing the pathogenic bacterium Xanthomonas oryzae pv. oryzae (Xoo) approximately 12-fold more potent than control bismerthiazol, in terms of their EC50 values (7.2 versus 89.8 μg/mL). Importantly, the most active compound 6b turned out to be one with the highest hydrophilicity and the lowest molecular weight within the series. In vivo bioassays further showed the application prospect of 6b as a promising plant bactericide for controlling Xoo. Additionally, in vitro antifungal activities of these compounds were also evaluated at the concentration of 50 μg/mL. Overall, the present study demonstrated the potential of 1,2,4-triazolo[4,3-a]pyridine-bearing quinazoline thioether derivatives as efficient agricultural antibacterial agents for crop protection.
- Fan, Zhijiang,Shi, Jun,Luo, Na,Ding, Muhan,Bao, Xiaoping
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p. 11598 - 11606
(2019/10/19)
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- Metal-Ligand Cooperative Approach to Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3 H)-ones under Mild Aerobic Conditions
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A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.
- Das, Siuli,Sinha, Suman,Samanta, Deepannita,Mondal, Rakesh,Chakraborty, Gargi,Branda?, Paula,Paul, Nanda D.
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p. 10160 - 10171
(2019/08/20)
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- “On-water” synthesis of quinazolinones and dihydroquinazolinones starting from O-bromobenzonitrile
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A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.
- Liu, Zibin,Zeng, Li-Yan,Li, Chao,Yang, Fubiao,Qiu, Fensheng,Liu, Shuwen,Xi, Baomin
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supporting information
(2018/09/26)
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- A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones
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The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N-dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc)2] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent yields. The new heterogeneous palladium catalyst can easily be prepared by a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution, and recycled up to eight times without significant loss of activity.
- You, Shengyong,Huang, Bin,Yan, Tao,Cai, Mingzhong
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- Method for synthesizing 2-phenyl quinazolinone compound from diphenyl acetylene compound as raw material
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The invention discloses a method for synthesizing a 2-phenyl quinazolinone compound from a diphenyl acetylene compound as raw material. The method comprises the following step: under coactions of a palladium catalyst, ligand and oxygen, enabling a diphenyl acetylene compound and 2-aminobenzene formamide as raw materials to react, thereby obtaining the 2-phenyl quinazolinone compound, wherein the reaction temperature is 60-110 DEG C; the reaction equation is as shown in the specification, in the formula, R is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, nitryl or methoxyl. The method has the beneficial effects that the raw material, namely the diphenyl acetylene compound, is cheap and easy to obtain, so that the method is relatively economic; the preparation process is simple and convenient to operate, and the obtained product is easy to treat and applicable to large-scale industrial production; no high temperature or high pressure is needed, and reaction conditions are gentle; the reaction time is short, the reaction is efficient, the yield is high, and relatively high reaction efficiency can be achieved after the reaction is amplified.
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Paragraph 0097-0099
(2018/07/06)
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- Bismuth-catalyzed synthesis of 2-substituted quinazolinones
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The bismuth-catalyzed oxidative condensation of aldehydes with 2-aminobenzamide under aerobic conditions is reported using ethanol as the solvent. Good to excellent isolated yields (68–95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The quinazolinones were further functionalized to afford N-allylated quinazolinones, 2-aminopyridine derivatives, and annulated polyheterocyclic compounds via transition-metal catalyzed reactions.
- Vemula, Sandeep R.,Kumar, Dinesh,Cook, Gregory R.
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supporting information
p. 3801 - 3805
(2018/09/18)
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- Method for synthesis of quinazolinone derivative
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The invention discloses a method for synthesis of quinazolinone; the method comprises the steps of starting from o-aminobenzamide, taking water as a solvent, carrying out a ring-enlargement reaction with benzaldehyde, to generate a dihydroquinazolinone intermediate, and then under participation of a metal iridium complex, dehydrogenating to obtain the quinazolinone derivative; the reaction shows three remarkable advantages: 1) the reaction is carried out in an aqueous solution so as to reduce use of a large amount of organic solvents, and water is a cheap, green and safe solvent; 2) the reaction avoids use of highly toxic oxidants, so as to avoid damage to the environment; and 3) hydrogen gas generated from the reaction is a by-product, and has no environmental pollution; therefore, the reaction accords with the requirements of green chemistry, and has broad prospects for development.
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- Potential anti-proliferative agents from 1,4-benzoxazinone-quinazolin-4(3H)-one templates
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A novel synthetic protocol has been developed for the synthesis of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids 7a–n by employing Pd-catalyzed C[sbnd]H arylation in presence of 5–10% phosphine ligand in good to excellent yields and evaluated for their anti-proliferative activity against three cancer cell lines such as A549 (lung), HeLa (cervical), MDA-MB-231 (breast). Compounds 7d, 7f, 7l and 7n exhibited promising anti-proliferative activity with GI50 values ranging from 0.37 to 2.73 μM respectively against A549, HeLa, and MDA-MB-231, while compound 7f showed significant activity against MDA-MB-231 with GI50 value 0.58 μM, 7j showed significant activity against A549 with GI50 value 0.32 μM and 7l showed significant activity against HeLa with GI50 value 0.37 μM. This is the first report on the synthesis and in vitro anti-proliferative evaluation of 1,4-benzoxazinone-acetylphenylallyl quinazolin-4(3H)-one hybrids.
- Bollu, Rajitha,Banu, Saleha,Kasaboina, Suresh,Bantu, Rajashaker,Nagarapu, Lingaiah,Polepalli, Sowjanya,Jain, Nishant
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supporting information
p. 5481 - 5484
(2017/11/03)
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- A copper catalyzed multicomponent cascade redox reaction for the synthesis of quinazolinones
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A copper catalyzed multicomponent cascade redox reaction for the synthesis of various quinazolinones starting from easily available 2-bromobenzamides, benzylic alcohols and sodium azide as a nitrogen source has been developed. The reaction involves copper catalyzed azidation of 2-bromobenzamide via an SNAr reaction and oxidation of benzyl alcohol followed by sequential reduction-condensation-oxidation to produce quinazolinones.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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p. 52884 - 52887
(2016/06/14)
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- Synthesis of quinazolinones from o-aminobenzamides and benzyl amines under metal-free conditions
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A convenient and transition-metal free protocol for quinazolinones synthesis with o-aminobenzamides and benzyl amines as substrates has been developed. Using H2O2 as the oxidant, various quinazolinones were obtained in moderate to good yields under metal- and additive-free conditions.
- Qi, Xin-Xin,Song, Zhen-Zhen,Gong, Jin-Long,Fang, Zheng-Yu,Wu, Xiao-Feng
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- One-Pot Copper(I)-Catalyzed Ligand/Base-Free Tandem Cyclooxidative Synthesis of Quinazolinones
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A novel and efficient Cu(I)-catalyzed ligand- and base-free multipathway domino strategy has been developed for the synthesis of 2-substituted quinazolinones. The reaction utilizes 2-bromobenzamide and multiform substrates such as aldehydes, alcohols, and methyl arenes for a one-pot protocol, whereas TMSN3 is used as a nitrogen source. A wide range of substrate scope, functional group tolerance, and operational simplicity are synthetically useful features.
- Upadhyaya, Kapil,Thakur, Ravi Kumar,Shukla, Sanjeev K.,Tripathi, Rama Pati
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p. 5046 - 5055
(2016/07/06)
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- Bimetallic Cu–Mn-Catalyzed Synthesis of 2-Arylquinazolin-4(3H)-ones: Aqueous Ammonia as Source of a Ring Nitrogen Atom
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A new method for the synthesis of 2-arylquinazolin-4(3H)-ones that involves a three-component coupling reaction of 2-bromobenzamide, aryl aldehydes, and aqueous ammonia has been developed. This protocol employs Cu–Mn spinel oxide as a heterogeneous catalyst and does not require the presence of a ligand or external oxidant. Key features of the reaction include a recyclable catalyst, ligand-free conditions, and a wide scope of possible substrates. The mechanism begins with the replacement of the bromine atom with NH2from aqueous ammonia followed by imine formation, intramolecular ring cyclization (C–N bond formation), and aromatization.
- Sharma, Rohit,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 5227 - 5233
(2016/11/13)
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- A facile vanadium-catalyzed aerobic oxidative synthesis of quinazolinones from 2-aminobenzamides with aldehydes or alcohols
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An efficient and simple VO(acac)2-catalyzed approach to the synthesis of quinazolinones has been developed. Various substituted quinazolinones have been synthesized from 2-aminobenzamides with alcohols or aldehydes in good to excellent yields with molecular oxygen as the oxidant. The process can also be scaled up.
- Bie, Zhixing,Li, Guosong,Wang, Lianyue,Lv, Ying,Niu, Jingyang,Gao, Shuang
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supporting information
p. 4935 - 4938
(2016/10/21)
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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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- Quinazolinones-Phenylquinoxaline hybrids with unsaturation/saturation linkers as novel anti-proliferative agents
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A new series of novel quinazolinones with allylphenyl quinoxaline hybrids 9a-n were efficiently synthesized in good yields by the reaction of 3-allyl-2-methylquinazolin-4(3H)-one (5a-n) with bromophenyl)quinoxaline (8) utilizing Pd catalyzed Heck-cross coupling and evaluated for anti-proliferative activity against four cancer cell lines such as HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). Compounds 9a, 9e, 9g and 9h exhibited promising anti-proliferative activity with GI50 values ranging from 0.06 to 0.2 μM against four cell lines, while compounds 9e and 9k showed significant activity against HeLa and MIAPACA cell lines and compounds 9b, 9d, 9h and 9j showed selective potency against IMR32 and MDA-MB-231 cell lines. This is the first report on the synthesis and in vitro anti-proliferative evaluation of E-2-(4-substituted)-3-(3-(4-(quinoxalin-2-yl)phenyl)allyl)quinazolin-4(3H)-ones (9a-n). Docking results indicate a sign of good correlation between experimental activity and calculated binding affinity (dock score), suggesting that these compounds could act as promising DNA intercalates.
- Palem, Jyothsna Devi,Alugubelli, Gopi Reddy,Bantu, Rajashaker,Nagarapu, Lingaiah,Polepalli, Sowjanya,Jain, S. Nishanth,Bathini, Raju,Manga, Vijjulatha
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supporting information
p. 3014 - 3018
(2016/06/13)
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- Copper-Catalyzed Synthesis of 2-Arylquinazolinones from 2-Arylindoles with Amines or Ammoniums
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A novel copper-catalyzed synthesis of quinazolinones from easily available 2-arylindoles and amines or ammoniums has been developed, which provided various quinazolinones in up to 99% yields for 43 examples. This strategy features tolerance of a wide range of functional groups, easily available starting materials, simple operation, mild reaction conditions, and environmental friendliness.
- Feng, Yadong,Li, Yudong,Cheng, Guolin,Wang, Lianhui,Cui, Xiuling
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p. 7099 - 7107
(2015/07/28)
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- Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine
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This study reports a safe, mild, and environmentally benign synthetic method toward 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamides through a cyclization-oxidation sequence using a catalytic amount of iodine, which serves as both a Lewis acid and an oxidant, harmless visible light irradiation, and molecular oxygen as the terminal oxidant.
- Nagasawa,Matsusaki,Nobuta,Tada,Miura,Itoh
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p. 63952 - 63954
(2015/08/18)
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- Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones
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We have developed a KOH-promoted transition-metal-free synthesis of 2-substituted 4(3H)-quinazolinones from anthranilamides and benzyl alcohols or cinnamyl alcohol with air as oxidant. The protocol is simple, practical, and cost saving. Graphical abstract: [Figure not available: see fulltext.]
- Qiu, Dezhi,Wang, Yanyan,Lu, Dongming,Zhou, Lihong,Zeng, Qingle
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p. 1343 - 1347
(2015/08/18)
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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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- Palladium-Catalyzed Carbonylative Reactions of 1-Bromo-2-fluorobenzenes with Various Nucleophiles: Effective Combination of Carbonylation and Nucleophilic Substitution
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systematic study on the carbonylative transformation of 1-bromo-2-fluorobenzenes with various nucleophiles has been performed. Different types of double nucleophiles, such as N-N, N-C, O-C, and N-S, can be effectively applied as coupling partners. The cor
- Chen, Jianbin,Natte, Kishore,Neumann, Helfried,Wu, Xiao-Feng
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supporting information
p. 16107 - 16110
(2015/01/09)
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- Palladium-catalyzed one-pot synthesis of quinazolinones via tert-butyl isocyanide insertion
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A novel palladium-catalyzed three-component reaction for the synthesis of quinazolin-4(3H)-ones from readily available 2-aminobenzamides and aryl halides via a palladium-catalyzed isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs quinazolin-4(3H)-ones in moderate to excellent yields with the advantages of operational simplicity.
- Jiang, Xiao,Tang, Ting,Wang, Jin-Mei,Chen, Zhong,Zhu, Yong-Ming,Ji, Shun-Jun
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p. 5082 - 5087
(2014/06/23)
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- TANKYRASE INHIBITORS
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The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.
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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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- Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction
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A cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides through a palladium-catalyzed carbonylation reaction has been developed. Various quinazolinones were produced in moderate to excellent yields. The reactions go through aminocarbonylation of aryl bromides-hydration of nitriles-cyclization sequence. Notably, all the products were isolated by recrystallization.
- Li, Haoquan,He, Lin,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 1336 - 1343
(2014/03/21)
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- Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes
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An interesting procedure for the zinc-catalyzed oxidative transformation of ready available 2-aminobenzamide, 2-aminobenzenesulfonamide with benzyl alcohols has been developed. Various quinazolinones and benzothiadiazine 1,1-dioxides were prepared in moderate to good yields under identical conditions. The reactions of both aromatic aldehydes and aliphatic aldehydes with 2-aminobenzamide under catalyst free conditions were described as well. In water media, the products were formed in good yields.
- Sharif, Muhammad,Opalach, Julita,Langer, Peter,Beller, Matthias,Wu, Xiao-Feng
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- Copper-catalyzed domino synthesis of quinazolin-4(3 H)-ones from (Hetero)arylmethyl halides, bromoacetate, and cinnamyl bromide
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Alkyl halides, including heteroarylmethyl and arylmethyl halides, bromoacetate, and cinnamyl bromide, are readily prepared via halogenation from basic raw materials, even using green processes. It is essential to replace their downstream products with them to prepare medicinally important heterocycles quinazolin-4(3H)-ones. Copper(I) bromide catalyzed domino reaction of alkyl halides and anthranilamides under air affords 2-substituted quinazolin-4(3H)-ones in good to excellent yields and with wide functional group tolerance. A mechanism for a copper(I) bromide involved organometal-catalyzed reaction via a four-step domino reaction is proposed. Georg Thieme Verlag Stuttgart New York.
- Wei, Haidong,Li, Tianbin,Zhou, Yue,Zhou, Lihong,Zeng, Qingle
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p. 3349 - 3354
(2014/01/06)
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