17629-01-5Relevant articles and documents
Palladium(II)-Catalyzed Three-Component Tandem Cyclization Reaction for the One-Pot Assembly of 4-Arylquinazolines
Wang, Zijuan,Chen, Wenteng,He, Chang,Zhang, Guolin,Yu, Yongping
, p. 1356 - 1364 (2020/11/09)
A one-pot method for joining three separate components leading to an assortment of 4-arylquinazolines (27 examples) in good to excellent yields is described. The method consists of a palladium(II)-catalyzed?-cascade reaction involving C(sp)-C(sp 2/s
Transition metal complex, polymer, mixture, composition and organic electronic device
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Paragraph 0296; 0300-0302, (2021/06/22)
The invention discloses a transition metal complex, a polymer, a mixture, a composition and an organic electronic device. According to the transition metal complex provided by the invention, because the transition metal complex contains an ester group and a relatively stable six-membered ring structure, the complex has excellent electron transmission capability, and can improve the luminous efficiency and prolong the service life of the device when being used as a luminescent layer doping material in an organic electronic device, especially an OLED (Organic Light Emitting Diode).
Preparation of 4-arylquinazolines with: O-(N-alkyl, N-p-tosyl)aminobenzonitriles, aryllithiums, and NIS
Naruto, Hiroki,Togo, Hideo
, p. 5666 - 5676 (2020/08/21)
The treatment of o-(N-alkyl,N-p-tosyl)aminobenzonitriles with aryllithiums, followed by the reaction with water, NIS under irradiation with a fluorescent lamp, and then tBuOK gave 2-alkyl-4-arylquinazolines or 4-arylquinazolines in good to moderate yields. The present reaction proceeds through the formation of N-iodoimines from imines with NIS, the generation of iminyl radicals, the 1,6-H shift by iminyl radicals, the cyclization via 6-exo-tet mode, and finally the elimination of p-toluenesulfinate to generate 2-alkyl-4-arylquinazolines or 4-arylquinazolines.
Copper-catalyzed oxidative amination of methanol to access quinazolines
Satish, Gandhesiri,Polu, Ashok,Kota, Laxman,Ilangovan, Andivelu
, p. 4774 - 4782 (2019/05/24)
A novel method for the copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram scale and its synthetic utility is demonstrated by synthesizing quazodine, a muscle-relaxing drug in high yields.
New Strategy for the Synthesis of Heterocycles via Copper-Catalyzed Oxidative Decarboxylative Amination of Glyoxylic Acid
Niu, Bin,Li, Shaoqing,Cui, Chang,Yan, Yizhe,Tang, Lin,Wang, Jianyong
supporting information, p. 7800 - 7803 (2019/11/28)
A copper-catalyzed oxidative decarboxylative amination of glyoxylic acid with substrates having two nitrogen-nucleophilic sites was first demonstrated. Using this novel approach, 1,3,5-triazines, quinazolinones and quinazolines were obtained in up to 93 % yields. Notably, glyoxylic acid was employed as the C1 synthon for heterocycles. This strategy enriches the application of glyoxylic acid for the synthesis of valuable heterocycles.
“On-Water” Palladium-Catalyzed Tandem Cyclization Reaction for the Synthesis of Biologically Relevant 4-Arylquinazolines
Yuan, Shuo,Yu, Bin,Liu, Hong-Min
, p. 13109 - 13113 (2019/10/22)
The quinazoline scaffold is prevalent in pharmaceutically relevant molecules that show diverse biological activities. Herein, we report an efficient “on-water” palladium-catalyzed tandem cyclization reaction from commercially available arylboronic acids and benzonitriles that enable the rapid access to 4-arylquinazoline scaffolds in good to excellent yields (45 examples, up to 98 % yield). This protocol has shown good functional group tolerance and broad substrate scope. The reaction was also performed on a gram scale and successfully applied to the synthesis of the highly potent and selective PI3Kδ inhibitor N11, showing the practicability and synthetic utility of the protocol. In this reaction, the quinazoline scaffold is efficiently constructed with the simultaneous formation of one C?C bond and one C?N bond. Collectively, the protocol could serve as an alternative strategy to synthesize biologically important quinazoline scaffolds.
4-arylquinazoline compounds and preparation method thereof
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Paragraph 0026-0029, (2019/09/17)
The invention provides 4-arylquinazoline compounds which have a general formula as shown in the specification, wherein R represents hydrogen, halogen, alkane, nitro or alkoxy, R represents hydrogen or methyl, Ar represents groups as shown in the specification, and R represents hydrogen, halogen, alkane, alkoxy, nitro, hydroxy, trifluoromethyl, phenyl or methoxycarbonyl; the compounds enrich the structures of 4-arylquinazoline compounds, and provide a material basis for further study on the potential biological activity of the compounds. The invention also provides a preparation methodof the compounds, which comprises the following step: cyanophenyl raw materials react with aromatic phenylboronic acid ArB(OH)2 in a sealed environment under the action of a palladium salt catalyst,a bidentate chelating ligand, a Lewis acid and a solvent at 30-300 DEG C to form the 4-arylquinazoline compounds; a structural formula of the 4-arylquinazoline compounds is shown in the specification,and the preparation method provided by the invention has the advantages of no need of inert gas protection, mild reaction conditions, short reaction time, high yield and the like.
Access to a Cationic, Electron-Poor N-Heterocyclic Carbene with a Quinazolinium Core by Postsynthetic Modification of Related Neutral Derivatives
Brüggemann, Peter,Wahl, Michaela,Schwengers, Sebastian,Buhl, Hannes,Ganter, Christian
, p. 4276 - 4286 (2018/12/04)
Derivatives of cationic six-membered N-heterocyclic carbene G with a quinazolinium scaffold are easily obtained by abstraction of an alcoholate group from related neutral precursors which are easily accessible. On the basis of this route, chalcogene adducts and metal complexes of G, which is a benzo-anellated pyrimidiniumylidene, could be prepared. Evaluation of the ligand properties by IR and 77Se NMR spectroscopy indicate that cationic carbene G is a much more powerful π-acceptor (δ(77Se): 768 ppm) and a significantly weaker overall donor (TEP: 2073 cm-1) than related neutral carbene 4 (361 ppm, 2054 cm-1). DFT calculations provide a rationale for these experimental observations. AuCl complexes of both carbenes were used as catalysts for the cyclization of a propargylamide to a methyleneoxazoline. The complex containing the cationic carbene featured a much higher activity.
Metal organic complex and organic light emitting device thereof
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Paragraph 0105; 0107, (2018/10/19)
The invention discloses a metal organic complex and an organic light emitting device thereof, and relates to the technical field of organic photoelectric materials. The complex has a structure as shown in a formula (I), an electron-rich dinitrogen coordination structure in a complex structure helps to stabilize central trivalent metal cations and can affect electronic cloud distribution on metal iridium, so that photoelectric properties of an integrated complex molecule are greatly affected, a ligand with the dinitrogen coordination structure and a metal four-membered ring have high rigidity,unnecessary vibration energy loss is reduced, and efficient light emitting performance is achieved. The complex has better heat stability and chemical properties by adjusting a substitutional group. The complex is prepared into the device and serves as a doping material, so that the device has the advantages of low driving voltage and high light emitting efficiency and is superior to an existing common OLED (organic light-emitting diode) device.
Silver-Catalyzed Isocyanide Insertion into N?H Bond of Ammonia: [5+1] Annulation to Quinazoline Derivatives
Zhang, Lingjuan,Li, Juanjuan,Hu, Zhongyan,Dong, Jinhuan,Zhang, Xian-Ming,Xu, Xianxiu
supporting information, p. 1938 - 1942 (2018/04/02)
A silver-catalyzed [5+1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields, respectively. The domino process involved an unprecedented isocyanide insertion into the N?H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions. (Figure presented.).
