- Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO
-
A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.
- Wen, Simiaomiao,Du, Yifan,Liu, Yiwen,Cui, Xiaofeng,Liu, Qixing,Zhou, Haifeng
-
-
- Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution
-
The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.
- Hou, Huiqing,Ma, Xinhua,Lin, Yingying,Lin, Jin,Sun, Weiming,Wang, Lei,Xu, Xiuzhi,Ke, Fang
-
p. 17721 - 17726
(2021/05/29)
-
- Method for preparing 2 -phenyl quinazolinone compound
-
The invention relates to a preparation method of 2 -phenyl quinazolinone compounds, in particular to II. To the method, 2 - (benzylamino) benzamide compound (I) is used as a raw material for reaction of the experiment model, a simple substance iodine cata
- -
-
Paragraph 0027-0029
(2021/10/30)
-
- An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols
-
An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.
- Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli
-
supporting information
p. 15344 - 15349
(2021/09/07)
-
- One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water
-
Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.
- Rao, Mugada Sugunakara,Hussain, Sahid
-
-
- Green synthesis method and application of quinazolinone compound
-
The invention discloses a green synthesis method and application of a quinazolinone compound. The structure of the quinazolinone compound is shown as a formula I, the preparation method comprises the following steps: by taking an R1-substituted hexafluoroisopropanol 2-aminobenzoate compound and R2-substituted amidine hydrochloride as raw materials, alkali as an additive, and acetonitrile, dioxane, tetrahydrofuran, DMSO (dimethylsulfoxide) or DMF (dimethyl formamide) as a solvent, reacting at normal temperature to generate the quinazolinone compound shown in the formula I. The method provided by the invention has the advantages of no need of heating, no need of using a metal catalyst, mild reaction conditions, no generation of by-products in the reaction, 100% conversion of the raw materials and simple post-treatment process, can be used to obtain the high-purity quinazolinone product, and is a simple green synthesis method; and the quinazolinone compound has high antitumor activity, and can be used for preparing antitumor drugs.
- -
-
Paragraph 0032; 0043-0044; 0047
(2021/04/07)
-
- Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones fromo-nitrobenzamide and alcohols
-
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
-
p. 13119 - 13123
(2021/04/22)
-
- Pd/C Catalyzed Cascade Synthesis of 2-Arylquinazolinones from 2-Iodoacetanilides Employing Ammonia and CO Precursors
-
An efficient and straightforward approach has been demonstrated for 2-aryl quinazolinones synthesis from 2-iodoacetanilides using ammonium carbamate/ammonium carbonate and oxalic acid under heterogeneous Pd/C catalyzed conditions. Herein, we have carried
- Shaifali,Mehara, Pushkar,Kumar, Ashish,Das, Pralay
-
p. 2459 - 2464
(2021/03/31)
-
- Ruthenium(II)-catalyzed C?C/C?N coupling of 2-arylquinazolinones with vinylene carbonate: Access to fused quinazolinones
-
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
-
supporting information
p. 995 - 999
(2021/03/03)
-
- Metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates at room temperature
-
Herein, we describe the novel reactivity of hexafluoroisopropyl 2-aminobenzoates. The metal-free synthesis of 1,4-benzodiazepines and quinazolinones from hexafluoroisopropyl 2-aminobenzoates has been developed at room temperature. These procedures feature
- Chen, Jiewen,Liang, En,Shi, Jie,Wu, Yinrong,Wen, Kangmei,Yao, Xingang,Tang, Xiaodong
-
p. 4966 - 4970
(2021/02/06)
-
- Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation
-
An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.
- Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar
-
supporting information
p. 2643 - 2648
(2021/02/16)
-
- Electrochemically induced synthesis of quinazolinonesviacathode hydration ofo-aminobenzonitriles in aqueous solutions
-
An efficient and practical electrochemically catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily availableo-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water play an unprecedented and vital role in the reaction. By electrochemically catalysed hydrolysis ofo-aminobenzonitriles, the synthesis of quinazolinones with benzaldehyde was first proposed. The synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactiveN-(2,5-dichlorophenyl)-6-(2,2,2-trifluoroethoxy) pteridin-4-amine, which enables straightforward, practical and environmentally benign quinazolinone formation.
- Yang, Li,Hou, Huiqing,Li, Lan,Wang, Jin,Zhou, Sunying,Wu, Mei,Ke, Fang
-
supporting information
p. 998 - 1003
(2021/02/16)
-
- Preparation method of quinazolinone derivative
-
The invention discloses a preparation method of a quinazolinone derivative, wherein the preparation method comprises the following steps: dissolving an anthranilonitrile compound represented by a formula I and an aldehyde represented by a formula II in a
- -
-
Paragraph 0087-0090
(2021/04/14)
-
- Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
-
A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
- Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
-
p. 1496 - 1501
(2021/05/03)
-
- Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
-
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
-
supporting information
p. 6831 - 6835
(2021/09/08)
-
- Electrochemical Synthesis of Quinazolinones by the Metal-Free and Acceptor-Free Dehydrogenation of 2-Aminobenzamides
-
An efficient approach has been developed for the construction of quinazolin-4(3 H)-ones by the selective anodic dehydrogenative oxidation/cyclization of benzylic chlorides and 2-aminobenzamides. The method features acceptor-free and metal-free dehydrogenation of amines to imines; a subsequent intermolecular addition provides the products in moderate to good yields.
- Yao, Yan,Meng, Xiu-Jin,Teng, Qing-Hu,Chen, Yan-Yan
-
supporting information
p. 1795 - 1799
(2020/09/07)
-
- Ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H)-ones: A convergent synthetic route to bouchardatine and sildenafil
-
A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra) in a highly convergent manner. This journal is
- Kim, Hun Young,Kim, Kyeongha,Oh, Kyungsoo
-
p. 31101 - 31105
(2020/09/23)
-
- A practical synthesis of quinazolinones via intermolecular cyclization between 2-halobenzamides and benzylamines catalyzed by copper(I) immobilized on MCM-41
-
The heterogeneous tandem N-arylation/oxidative C–H amidation of 2-halobenzamides and benzylamines was achieved in DMSO at 110 or 120 °C by using an MCM-41-immobilized L-proline copper(I) complex [MCM-41-L-Proline-CuBr] as the catalyst and air as the oxidant, yielding a variety of quinazolinone derivatives in good yields. The new MCM-41-L-Proline-CuBr catalyst can easily be prepared from commercially readily available and inexpensive reagents and recovered by filtration of the reaction mixture, and reused up to seven times with almost consistent activity.
- Yan, Nan,You, Chongren,Cai, Mingzhong
-
p. 161 - 169
(2019/07/12)
-
- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
-
A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
-
p. 3160 - 3170
(2019/08/07)
-
- 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
-
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
-
supporting information
p. 14506 - 14511
(2019/11/21)
-
- Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles
-
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
-
p. 3043 - 3048
(2019/03/17)
-
- A quinazolinone of heterocyclic compound synthetic method
-
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.
- -
-
Paragraph 0123-0126
(2019/07/01)
-
- Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3–H bond activation using a new metal-organic framework as catalyst
-
A new mixed-linker iron-based MOF VNU-21 [Fe3(BTC)(EDB)2·12.27H2O] was synthesized via mixed-linker synthetic strategy using 1,3,5-benzenetricarboxylic acid, 4,4′-ethynylenedibenzoic acid, and FeCl2. The VNU-21 was consequently used as a recyclable heterogeneous catalyst in the one-pot synthesis of quinazolinones via two steps under oxygen atmosphere. The synthetic scheme involved iron-catalyzed oxidative Csp3–H bond activation to achieve decarboxylation of phenylacetic acids, and succeeding metal-free oxidative cyclization with 2-aminobenzamides. The VNU-21 was more effective than a series of heterogeneous and homogeneous catalysts. It was possible to reutilize the iron-based framework without a considerable deterioration in catalytic performance. To our best knowledge, this one-pot synthesis of quinazolinones was not previously performed using a recyclable catalyst.
- To, Tuong A.,Vo, Yen H.,Nguyen, Hue T.T.,Ha, Phuong T.M.,Doan, Son H.,Doan, Tan L.H.,Li, Shuang,Le, Ha V.,Tu, Thach N.,Phan, Nam T.S.
-
-
- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
-
Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
-
-
- A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones
-
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
-
-
- Bismuth-catalyzed synthesis of 2-substituted quinazolinones
-
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.
-
supporting information
p. 3801 - 3805
(2018/09/18)
-
- Method for synthesis of quinazolinone derivative
-
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.
- -
-
Paragraph 0152-0154
(2017/04/20)
-
- Solvent-free copper-catalyzed three-component synthesis of 2-substituted quinazolin-4(3H)-ones
-
Abstract: A novel and efficient approach for the synthesis of quinazoline-4(3H)-ones through a one-pot copper-catalyzed three-component reaction of isatoic anhydrides, aryl nitriles, and ammonium acetate under solvent-free conditions in good yields is described. Graphical abstract: [Figure not available: see fulltext.]
- Soheilizad, Mehdi,Soroosh, Shakiba,Pashazadeh, Rahim
-
p. 739 - 743
(2017/03/17)
-
- Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant
-
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
-
p. 65196 - 65204
(2016/07/21)
-
- Formation of amides, their intramolecular reactions for the synthesis of N-heterocycles, and preparation of a marketed drug, sildenafil: A comprehensive coverage
-
A unified approach to the tandem preparation of diverse nitrogen heterocycles via decarboxylative acylation of ortho-substituted amines with α-oxocarboxylic acids and subsequent intramolecular cyclizations has been developed. The key features of this work include: the first example of transition-metal-free decarboxylative amidation of α-oxocarboxylic acids with ortho-substituted amines, realization of intramolecular cyclization of amides employing nucleophiles that have previously been unexplored, mechanistic investigation of an unprecedented K2S2O8 promoted amide formation and its subsequent intramolecular cyclizations, and application to the synthesis of a best-selling marketed drug.
- Laha, Joydev K.,Patel, Ketul V.,Satyanarayana Tummalapalli,Dayal, Neetu
-
supporting information
p. 10245 - 10248
(2016/08/23)
-
- Divergent Synthesis of Quinazolin-4(3H)-ones and Tryptanthrins Enabled by a tert-Butyl Hydroperoxide/K3PO4-Promoted Oxidative Cyclization of Isatins at Room Temperature
-
A synergetic tert-butyl hydroperoxide/K3PO4-promoted oxidative cyclization has been developed for the facile synthesis of various functionalized quinazolin-4(3H)-ones from commercially available isatins and amidine hydrochlorides at room temperature. The synthetic utility of this strategy was illustrated by the convenient synthesis of tryptanthrin derivatives via a self-dimerization of isatins under the same conditions.
- Jia, Feng-Cheng,Zhou, Zhi-Wen,Xu, Cheng,Wu, Yan-Dong,Wu, An-Xin
-
supporting information
p. 2942 - 2945
(2016/07/06)
-
- Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones
-
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
-
p. 1343 - 1347
(2015/08/18)
-
- Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydro quinazolinones and quinazolinones
-
The Y(OTf)3-catalyzed aerobic oxidative cyclization reaction for the selective synthesis of dihydroquinazolinones and quinazolinones has been developed. This method provides a practical, effective and green synthetic approach to dihydroquinazolinones and quinazolinones which both are important units in many biologically active compounds.
- Shang, Ying-Hui,Fan, Li-Yan,Li, Xiang-Xiong,Liu, Meng-Xia
-
supporting information
p. 1355 - 1358
(2015/10/28)
-
- Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
-
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
-
supporting information
p. 6471 - 6474
(2014/06/09)
-
- Palladium-Catalyzed Carbonylative Reactions of 1-Bromo-2-fluorobenzenes with Various Nucleophiles: Effective Combination of Carbonylation and Nucleophilic Substitution
-
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
-
supporting information
p. 16107 - 16110
(2015/01/09)
-
- Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction
-
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
-
supporting information
p. 1336 - 1343
(2014/03/21)
-
- Synthesis of 2-arylquinazolin-4(3H)-ones by N-aryl benzamidines with aromatic carbonates
-
The reaction of N-aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m, 1n with diphenyl carbonate 2a or ethyl phenyl carbonate 2b synthesized 2-arylquinazolin-4(3H)-ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n in simple and
- Aikawa, Shunichi,Sekiguchi, Chiharu,Yamazaki, Yuko,Hattori, Mika,Isaka, Tatsuya,Yoshida, Yasuhiko,Ihara, Shogo
-
p. 343 - 348
(2014/04/17)
-
- A simple one-pot synthesis of 2-substituted quinazolin-4(3 H)-ones from 2-nitrobenzamides by using sodium dithionite
-
A simple one-pot procedure for the preparation of 2-(het)arylquinazolin- 4(3H)-ones starting from readily available 2-nitrobenzamides and (het)aryl aldehydes is described. Sodium dithionite is used as the reducing agent for the nitro group, and its decomposition in situ in aqueous N,N-dimethylformamide leads to the final oxidation step that gives the desired heterocyclic compounds. Georg Thieme Verlag Stuttgart, New York.
- Romero, Angel H.,Salazar, Jose,Lopez, Simon E.
-
p. 2043 - 2050
(2013/07/26)
-
- Copper-catalyzed domino synthesis of quinazolin-4(3 H)-ones from (Hetero)arylmethyl halides, bromoacetate, and cinnamyl bromide
-
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
-
p. 3349 - 3354
(2014/01/06)
-
- One-pot tandem approach for the synthesis of quinazolinones from ortho-aminobenzamides, benzyl halides and benzyl alcohols
-
A one-pot tandem procedure is described for the synthesis of quinazolinones from benzyl halides or benzyl alcohols and ortho-aminobenzamides leading to the production of quinazolinones with high yields under mild conditions in DMSO without requiring an additional oxidant. According to the current method benzyl chlorides, benzyl bromides and benzyl alcohols bearing a range of substituents are suitable substrates.
- Motevalli, Kourosh,Mirzazadeh, Roghieh,Yaghoubi, Zahra
-
p. 701 - 702
(2013/02/23)
-
- One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers
-
A one-pot oxidative cyclization of primary alcohols with o-aminobenzamides to quinazolinones was successfully achieved using [Cp*IrCl 2]2 (Cp* = pentamethylcyclopentadienyl) as a catalyst under hydrogen transfer conditions.
- Zhou, Jianguang,Fang, Jie
-
supporting information; experimental part
p. 7730 - 7736
(2011/11/30)
-
- Copper-catalyzed domino synthesis of quinazolinones via Ullmann-type coupling and aerobic oxidative C-H amidation
-
An efficient copper-catalyzed approach to quinazolinone derivatives has been developed, and the protocol uses cheap and readily available substituted 2-halobenzamides and (aryl)methanamines as the starting materials as well as economical and environmentally friendly air as the oxidant. This can be the first example of constructing N-heterocycles via sequential Ullmann-type coupling under air and aerobic oxidative C-H amidation.
- Xu, Wei,Jin, Yibao,Liu, Hongxia,Jiang, Yuyang,Fu, And Hua
-
supporting information; experimental part
p. 1274 - 1277
(2011/04/24)
-
- A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
-
An effective one-pot three-component route to 4(3H)-quinazolinones from commercially available starting materials is reported. Thus, isatoic anhydride reacted with ammonium acetate or primary amines and aldehydes in the presence of iodine to produce the corresponding quinazolinone derivatives in moderate to good yields. Springer-Verlag 2010.
- Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Alizadeh, Mohsen
-
experimental part
p. 877 - 881
(2011/06/26)
-
- Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source
-
A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.
- Zhao, Haibo,Fu, Hua,Qiao, Renzhong
-
experimental part
p. 3311 - 3316
(2010/08/05)
-
- A novel, one-pot, solvent-, and catalyst-free synthesis of 2-aryl/alkyl-4(3H)-quinazolinones
-
A novel and one-pot synthesis of 2-aryl/alkyl-4(3H)-quinazolinones is described. The in situ prepared amidoximes from the reaction between nitriles and hydroxylamine are condensed with anthranilic acids under solvent- and catalyst-free conditions to produ
- Adib, Mehdi,Ansari, Samira,Mohammadi, Ali,Bijanzadeh, Hamid Reza
-
experimental part
p. 30 - 32
(2010/03/03)
-
- Microwave-assisted synthesis of quinazolinone derivatives by efficient and rapid iron-catalyzed cyclization in water
-
A green, rapid, and efficient method was developed for synthesizing quinazolinone derivatives from substituted 2-halobenzoic acids and amidines via microwave-assisted iron-catalyzed cyclization with or without ligand in water (methods A and B) or DMF (methods C and D). With these methods, moderate to high yields of the desired products can be obtained from even inactive substrates, such as guanidines. To the best of our knowledge, this is the first report on the synthesis of N-heterocyclic compounds by iron-catalyzed C-N coupling in aqueous media. The Royal Society of Chemistry 2009.
- Zhang, Xiaodong,Ye, Deju,Sun, Haifeng,Guo, Diliang,Wang, Jiang,Huang, He,Zhang, Xu,Jiang, Hualiang,Liu, Hong
-
experimental part
p. 1881 - 1888
(2011/02/27)
-
- A new efficient method for the three-component synthesis of 4(3H)-Quinazolinones
-
4(3H)-Quinazolinones were efficiently synthesised by the three component cyclisation-oxidation of isatoic anhydride, ammonium acetate and aromatic aldehydes in the presence of ceric ammonium nitrate in ethanol. The Japan Institute of Heterocyclic Chemistry.
- Baghbanzadeh, Mostafa,Dabiri, Minoo,Salehi, Peyman
-
experimental part
p. 2809 - 2815
(2011/04/17)
-
- Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones
-
A series of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones have been synthesized in good to excellent yields and high selectivity by one-pot reaction using isatoic anhydride, ammonium acetate (or amines), and aldehydes in ethanol or in DMSO under mild conditions, respectively. The reaction was efficiently promoted by 1 mol % Ga(OTf)3 and the catalyst could be recovered easily after the reactions and reused without evident loss of reactivity.
- Chen, Jiuxi,Wu, Dengze,He, Fei,Liu, Miaochang,Wu, Huayue,Ding, Jinchang,Su, Weike
-
p. 3814 - 3818
(2008/09/21)
-
- Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives
-
We have developed a general and highly efficient copper-catalyzed method for synthesis of quinazoline and quinazolinone derivatives, the target products were obtained in good to excellent yields via cascade reactions of amidine hydrochlorides with substituted 2-halobenzaldehydes, 2-halophenylketones, or methyl 2-halobenzoates, and the method is of simple, economical and practical advantages. The Royal Society of Chemistry 2008.
- Huang, Cheng,Fu, Yuan,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
-
supporting information; experimental part
p. 6333 - 6335
(2009/04/13)
-
- A novel one-pot synthesis of 2-aryl-4(3H)-quinazolinones using room temperature ionic liquid as reaction medium as well as promoter
-
An efficient one-pot synthesis of 2-aryl-4(3H)-quinazolinones from 2-amino benzamides and substituted benzoyl chlorides in a room temperature ionic liquid is described. Compared with the classical reaction conditions, this new synthetic method has the advantages of recyclability of ionic liquid, very good to excellent yields (78-92%), the absence of hazardous and expensive catalysts, and easy workup procedures giving rise to a process with minimum waste.
- Potewar,Nadaf,Daniel, Thomas,Lahoti,Srinivasan
-
p. 231 - 241
(2007/10/03)
-