- Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
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A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
- Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
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supporting information
p. 1427 - 1431
(2020/11/02)
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- Effect of Fe(iii)-based MOFs on the catalytic efficiency of the tandem cyclooxidative reaction between 2-aminobenzamide and alcohols
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The catalytic properties of metal-organic frameworks (MOFs) containing triangular Fe(iii) clusters in the promotion of organic syntheses and photocatalysis applications have been receiving substantial attention for decades. These clusters are appealing due to the strong Lewis acidity afforded by coordinatively unsaturated sites upon the removal of solvent from the framework. In this paper, triangular Fe(iii) cluster-based MOFs were shown to be highly efficient heterogeneous catalysts for the solvent-free one-pot condensation of 2-aminobenzamide and alcohols to form quinazolin-4-ones under microwave irradiation. The Fe-MOF catalysts ranging from microporous to mesoporous structures with a variety of geometrical pore structures were investigated. Because of the open accessible spaces for reactants and high density of active sites, MOF-907, built from trimer Fe clusters and a mixture of two linkers, was more effective than other Fe(iii)-MOFs. The catalyst can be used for a broad substrate scope and recycled several times without a significant drop-off in its activity.
- Dang, Minh-Huy Dinh,Nguyen, Trang Thi Minh,Nguyen, Linh Ho Thuy,Nguyen, Trang Thi Thu,Phan, Thang Bach,Tran, Phuong Hoang,Doan, Tan Le Hoang
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supporting information
p. 14529 - 14535
(2020/10/02)
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- Commercial Copper-Catalyzed Aerobic Oxidative Synthesis of Quinazolinones from 2-Aminobenzamide and Methanol
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The focus of this study was the development of a new synthetic method for quinazolinones based on the principles of Green Chemistry. Quinazolinones were synthesized from 2-aminobenzamide using methanol as both the C1 source and a green solvent in the presence of base Cs2CO3. Additionally, a commercially available, economical copper complex was used as a catalyst in the reaction. The desired products were achieved in moderate to high yield with up to 99 % isolated yield.
- Chatwichien, Jaruwan,Choommongkol, Vachira,Kerdphon, Sutthichat,Meepowpan, Puttinan,Rithchumpon, Puracheth,Sanghong, Patthadon,Singh, Thishana
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supporting information
p. 2730 - 2734
(2020/05/18)
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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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- Method for preparing quinazolinone from enol
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The invention discloses a method for preparing a quinazolinone derivative from enol. According to the method, a relatively inexpensive ruthenium complex is used as a catalyst in a reaction to catalyzea microwave reaction of commercial and easily-available 2-aminobenzamide with enol for the preparation of quinazolinone. Compared with conventional synthesis methods for quinazolinone of the same kind, the method of the invention has the following advantages: no alkali is used in the reaction process; clean and non-toxic tetrahydrofuran is used as a reaction solvent; hydrogen is automatically transferred, and the atom economy of the reaction is high; and the by-product of the invention is only water.
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Paragraph 0119-0123
(2019/03/15)
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- Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters
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Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.
- Gavin, Joshua T.,Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues
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A general metal-free oxidative cyclization process has been developed for the synthesis of quinazolinones, benzothiadiazines and quinazolines. By this protocol, a range of substituted 2-aminobenzamides, 2-aminobenzenesulfonamide and 2-(aminomethyl)anilines react with various alcohols, leading to the desired annulated products smoothly. This protocol features many advantages as broad substrate scope, mild reaction conditions, low environmental pollution, high atom-economy and good to excellent yields.
- Sun, Jinwei,Tao, Tao,Xu, Dan,Cao, Hui,Kong, Qinggang,Wang, Xinyu,Liu, Yun,Zhao, Jianglin,Wang, Yi,Pan, Yi
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p. 2099 - 2102
(2018/05/04)
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- Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl
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Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.
- Kang, Huaiyuan,Wang, Weili,Sun, Qinqiang,Yang, Shuya,Jin, Juan,Zhang, Xuewen,Ren, Xiaoliang,Zhang, Jiming,Zhou, Jianhua
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p. 293 - 296
(2018/11/27)
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- The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX
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Performing any synthesis using several arylamines and hypervalent iodine(V) reagents by direct mixing is unrealistic because of the high exothermic reaction or explosion. Herein we demonstrate, when anilines were substituted with an amide group at the orthoposition, successful chemical reactions could be performed due to intramolecular control. At maximum contact of the reacting substances, i.e., under solvent-free mechanochemical conditions, 2-aminobenzamides, aryl-, alkylaldehydes and the iodine(V) reagent o-iodoxybenzoic acid (IBX) led to substituted quinazolin-4(3H)-one derivatives in fair yields.
- Alam, Md Toufique,Maiti, Saikat,Mal, Prasenjit
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supporting information
p. 2396 - 2403
(2018/10/15)
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- Facile and solvent-free synthesis of quinazolin-4(3H)-ones under microwave condition promoted by SbCl3
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– Antimony trichloride (SbCl3) was found to be an effective catalyst (1 mol%) for one-pot synthesis of quinazolin-4(3H)-ones in good to excellent yields using anthranilamide and acyl chlorides under microwave irradiation. This method has the advantages of simplicity, mild reaction conditions, highly tolerant to several functional groups, as well as the avoidance of hazardous solvents.
- Li, Jun,Wang, Weili,Su, Xinglin,Zhang, Xiaoling,Zhang, Yan,Zhang, Xuewen,Cai, Mengmeng,Cao, Yuqian,Jin, Juan,Xu, Yanbin
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p. 2107 - 2110
(2019/04/04)
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- The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru-clusters/Ceria Catalyst
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Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru-clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H2O is generated as the only by-product. A series of quinazolinones with aromatic or non-aromatic substituents can be obtained in yields of up to 99 %. The Ru-clusters/ceria can be reused at least four times. The analysis of the E-factor (environmental impact factor) for the synthesis of 2-ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.
- An, Jinghua,Wang, Yehong,Zhang, Zhixin,Zhao, Zhitong,Zhang, Jian,Wang, Feng
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supporting information
p. 12308 - 12312
(2018/09/06)
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- Quinazolinone compound preparation method
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The present invention relates to a quinazolinone compound preparation method, wherein a quinazolinone-based compound is prepared by using 2-aminobenzamide, olefin and carbon monoxide as reaction substrates and using tetrahydrofuran as a solvent under the catalysis effect of a ruthenium loaded metal oxide. The reaction process comprises: adding tetrahydrofuran, 2-aminobenzamide, olefin and a catalyst into a pressure container, inflating with carbon monoxide, sealing, stirring, and carrying out a reaction for not less than 0.5 h at a reaction temperature of not lower than 120 DEG C, wherein thecatalyst is easily separated from the reaction system after the reaction, and can be recycled multiple times, and the yield of the quinazolinone-based compound is up to 100%.
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Paragraph 0075-0077
(2018/09/28)
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- Method for synthesizing quinazolinone from anthranilamide and unsaturated aldehyde
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The invention discloses a method for synthesizing quinazolinone from anthranilamide and unsaturated aldehyde. The method comprises the steps: adding the quinazolinone, a transition metal catalyst, methylbenzene and the unsaturated adhehyde in a reaction container, making a reaction mixture react under 110 to 120 DEG C for 10 to 12 hours and cooling to room temperature; then separating to obtain atarget compound. According to the method disclosed by the invention, the anthranilamide and the unsaturated aldehyde which are easy to obtain are utilized as beginning raw materials, only water is generated as a byproduct in reaction, and reaction atom economy is high; thus, the reaction meets a green chemical requirement and has a wide development prospect.
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Paragraph 0094-0097
(2018/03/24)
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- Sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives
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The invention discloses a sulfonic acid ionic liquid catalyzing controlled synthesis method for dihydro-quinazolinone and quinazolinone derivatives. The dihydro-quinazolinone and quinazolinone derivatives are controllably prepared through a cascade reaction of anthranilamide or derivatives thereof and an aldehyde compound by taking sulfonic acid ionic liquid as a catalyst. Under the set catalytic reaction condition, the conversion rate of raw materials reaches up to 99%, and the yield of dihydro-quinazolinone and the yield of quinazolinone both can reach 95%. Compared with the prior art, the green solvent-ionic liquid is taken as the catalyst, no additional oxidizing agent or heavy metal catalyst is needed, the advantages that the reaction conditions are mild, environmental friendliness is achieved, the reaction selectivity and the product yield are high, controllable synthesis is achieved, and the catalyst can be recycled and reused conveniently are achieved, and the novel method is friendly to environment and efficient in synthesis.
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Paragraph 0058; 0059; 0060; 0061; 0062
(2017/08/28)
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- New facile and solvent-free method for the one-pot synthesis of quinazolin-4(3H)-ones catalyzed by SbCl3 under microwave irradiation
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Efficient and fast condensation of anthranilic amide or anthranilic acid with various orthoesters have been carried out using a catalytic amount of Antimony(III) chloride (SbCl3) under microwave irradiation to afford a series of 2-substituted quinazolin-4(3H)-ones in good to excellent yields under solvent free condition. The reactions have been operated without solvent by one-pot reaction only in several minutes and the reactions have been optimized, such as microwave irradiation power and catalyst charge. Furthermore, ammonium acetate as a nitrogen source in the condition of anthranilic acid is very convenient. Its simplicity, efficiency, mild reaction conditions, high yields of products, easy workup procedure and good generality, make this one-pot procedure interesting for the preparation of different kinds of substituted quinazolin-4(3H)-ones. One of the important features of this methodology is the use of a minimum amount of SbCl3 as an effective Lewis acid catalyst and the avoidance of hazardous organic solvent.
- Wang, Wei-Li,Li, Xiao-Xia,Zhang, Tao,Zhang, Ji-Ming,Zhou, Jian-Hua
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p. 1196 - 1202
(2017/01/25)
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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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- The cascade synthesis of quinazolinones and quinazolines using an α-MnO2 catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant
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Heterogeneously catalyzed synthesis of quinazolinones or quinazolines is reported in this study. An α-MnO2 catalyst is found to be highly active and selective in the oxidative cyclization of anthranilamides or aminobenzylamines with alcohols using TBHP as an oxidant. This protocol exhibits a broad substrate scope, and is operationally simple without an additive.
- Zhang, Zhe,Wang, Min,Zhang, Chaofeng,Zhang, Zhixin,Lu, Jianmin,Wang, Feng
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supporting information
p. 9205 - 9207
(2015/06/02)
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- Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation
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A one-pot I2-mediated annulation reaction of substrates containing diamino groups and aldehydes has been developed via oxidative C-N bond formation. This general and environmentally benign synthetic approach provides facile access to a variety of 1,3-diazaheterocyclic compounds, including quinazolinones, benzimidazoles, and cyclic amidines.
- Tian, Xianhai,Song, Lina,Li, Ertong,Wang, Qiang,Yu, Wenquan,Chang, Junbiao
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p. 62194 - 62201
(2015/08/03)
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- Y(OTf)3-catalyzed heterocyclic formation via aerobic oxygenation: An approach to dihydro quinazolinones and quinazolinones
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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
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supporting information
p. 1355 - 1358
(2015/10/28)
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- Metal-free aerobic oxidative C-N bond cleavage of tertiary amines for the synthesis of N-heterocycles with high atom efficiency
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An efficient metal-free aerobic oxidative C-N bond cleavage of tertiary amines has been developed to construct N-heterocycles using molecular oxygen as the sole oxidant with high atom efficiency, in which all of the three alkyl groups in tertiary amines can be utilized and transformed into N-heterocycles. This journal is the Partner Organisations 2014.
- Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Han, Daoqing,Han, Li-Biao,Yin, Shuang-Feng
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supporting information
p. 3802 - 3807
(2014/06/09)
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- A Cu (NO3)2.3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles
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One pot synthesis of alkyl, aryl, heteroaryl mono(2)substituted 4(3H)-quinazolinones and 2-aryl or heteroaryl, 1-arylmethyl or heteroarylmethyl -1H-benzimidazoles using a water soluble Cu (NO3)2.3H 2O catalyst at room/ambient temperature in excellent yield.
- Durgareddy,Ravikumar,Ravi,Adapa, Srinivas R.
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p. 175 - 182
(2013/04/24)
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- Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate
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The iodine catalyzed one-pot two-step oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant has been achieved, providing a convenient and efficient method for the synthesis of quinazolinones in good to excellent yields via in situ oxidation of primary alcohols to aldehydes. The reaction was carried out in the green solvent DMC, under atmospheric conditions. The procedure is suitable for aromatic or alkyl primary alcohols. The Royal Society of Chemistry 2013.
- Ge, Wenlei,Zhu, Xun,Wei, Yunyang
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p. 10817 - 10822
(2013/09/02)
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- A simple and efficient approach to quinazolinones under mild copper-catalyzed conditions
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(Chemical Equation Presented) Cop some rings: A simple and highly efficient copper-catalyzed method for the synthesis of quinazolinone derivatives through the reaction of substituted 2-halobenzoic acids with amidines or guanidines under mild conditions ha
- Liu, Xiaowei,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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supporting information; experimental part
p. 348 - 351
(2009/04/14)
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- Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives
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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
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supporting information; experimental part
p. 6333 - 6335
(2009/04/13)
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- Benign and efficient synthesis of 2-substituted 4(3H)-quinazolinones mediated by iron(III) chloride hexahydrate in refluxing water
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Condensation of aldehydes with anthranilamide in refluxing water using iron(III) chloride hexahydrate as an oxidiant afforded 2-substituted 4(3H)-quinazolinones in good yields (77-93%). This method provides several advantages such as being environmentally friendly, having a simple work-up procedure, and affording high yields.
- Wang, Guan-Wu,Miao, Chun-Bao,Kang, Hui
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p. 1426 - 1430
(2007/10/03)
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