5428-24-0Relevant academic research and scientific papers
A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds
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Paragraph 0011; 0045, (2022/01/10)
The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr
Synthesis of 6-phenylbenzo[h]quinolinesviaphotoinduced dehydrogenative annulation of (E)-2-phenyl-3-styrylpyridines
He, Yun,Liang, Yong,Niu, Lixin,Wang, Tao,Xi, Jin,Zhang, Zunting
supporting information, p. 8554 - 8558 (2021/10/20)
A concise and environmentally friendly protocol was developed for the synthesis of 6-phenylbenzo[h]quinolines. 6-Phenylbenzo[h]quinolines were obtained in good yieldsviairradiation of (E)-2-phenyl-3-styrylpyridines with a 254 nm UV light (64 W) in EtOH under an argon atmosphere in the presence of TFA. The reaction is a dehydrogenative annulation reaction that proceeds through 6π-electrocyclization, a [1,5]-H shift, 1,3-enamine tautomerization, and elimination of a hydrogen molecule to afford 6-phenylbenzo[h]quinolines. The described protocol not only avoids the usage of a transition metal catalyst and an oxidant but also has the advantages of high atom efficiency and mild reaction conditions.
Synthesis of Benzoacridines and Benzophenanthridines by Regioselective Pd-Catalyzed Cross-Coupling Reactions Followed by Acid-Mediated Cycloisomerizations
Janke, Sophie,Boldt, Sebastian,Ghazargan, Karapet,Ehlers, Peter,Villinger, Alexander,Langer, Peter
, p. 6177 - 6197 (2019/08/16)
A convenient synthesis of various benzoacridines and benzophenanthridines from readily available dihalogenated quinolines is reported. The synthesis is based on regioselective Suzuki and Sonogashira reactions followed by Br?nsted acid-mediated cycloisomerization. The developed methodology is highly modular and allows the construction of various ring systems and substitution patterns in high yields. The optical and electrochemical properties of selected derivatives were investigated.
Direct arylation for the synthesis of 2-arylquinolines from N-methoxyquinoline-1-ium tetrafluoroborate salts and arylboronic acids
Ren, Xiaoxiao,Han, Shuaijun,Gao, Xianying,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
, p. 1065 - 1068 (2018/02/19)
A rapid and direct arylation reaction of N-methoxyquinoline-1-ium tetrafluoroborate derivatives and arylboronic acids with high regioselectivety at room temperature was discovered. The reaction shows exceptional functional group tolerance and broad substrate scope regarding both the quinoline derivatives and the arylboronic acids.
Organic photoelectric functional material, luminescent device, preparation method and application thereof
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Paragraph 0108; 0109; 0110; 0111, (2018/07/30)
The invention relates to the technical field of organic luminescent materials and particularly relates to an organic photoelectric functional material, a luminescent device, a preparation method and application thereof. The organic photoelectric functional material has electroluminescent and electron transmitting properties, and can be applied in the field of organic electroluminescence. The organic photoelectric functional material is selected from at least one of compounds shown in a formula I and a formula II. When the organic photoelectric functional material is used as an electroluminescent material, the luminescence of the organic photoelectric functional material can be regulated by using substitute groups to modify quinoline parts, and the luminescent interval is in the range from345nm to about 700nm. When the organic photoelectric functional material is used as an electron transmission type main body material and forms an exciplex common main body together with a hole-type main body material, the prepared luminescent device is improved in the aspects of stability and luminescence efficiency compared with the traditional main body material. The formulas are shown in the description.
TMEDA-assisted effective direct ortho arylation of electron-deficient N -heteroarenes with aromatic grignard reagents
Zhuo, Fang-Fang,Xie, Wen-Wen,Yang, Yong-Xin,Zhang, Lei,Wang, Pei,Yuan, Rui,Da, Chao-Shan
, p. 3243 - 3249 (2013/06/26)
In the addition of TMEDA in toluene, aryl Grignards could effectively and site-specifically ortho-arylate electron-deficient heteroarenes under mild conditions. This endeavor successfully changed the old low-yielding reaction, aryl Grignard addition to N-heteroarenes, into an efficient procedure for heterobiaryls. The combination of the inexpensive aryl Grignards, TMEDA, the cost-free air, no use of any transition-metal catalyst, the mild reaction conditions, and the high-yielding gram-scale results enables this new procedure to be cost-effective and potentially utilizable in industry.
Iron-catalyzed direct C-H arylation of heterocycles and quinones with arylboronic acids
Deb, Arghya,Manna, Srimanta,Maji, Arun,Dutta, Uttam,Maiti, Debabrata
supporting information, p. 5251 - 5256 (2013/09/02)
The arylation of C-H bonds to generate heteroaryl-aryl (Het-Ar) and arylated quinone (Quin-Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het-Ar and Quin-Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO 3)3. The C-arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use. Direct C-H arylation of a variety of heterocycles and quinones with arylboronic acids has been developed. An inexpensive iron catalyst, Fe(NO3)3, and a co-oxidant, persulfate, were used in air. The protocol is applicable for large-scale synthesis and is expected to find application as a result of its operational simplicity. Copyright
A method for the synthesis of substituted quinolines via electrophilic cyclization of 1-azido-2-(2-propynyl)benzene
Huo, Zhibao,Gridnev, Ilya D.,Yamamoto, Yoshinori
supporting information; experimental part, p. 1266 - 1270 (2010/04/29)
(Chemical Equation Presented) A new and efficient strategy for the synthesis of substituted quinolines via electrophilic cyclization is developed. The intramolecular cyclization of 1-azido-2-(2-propynyl)benzene 1 proceeds smoothly in the presence of electrophilic reagents (I2, Br 2 , ICl, NBS, NIS, and HNTf2) in CH3NO 2 at room temperature or in the presence of catalytic amounts of AuCl3/AgNTf2 in THF at 100 °C to afford the corresponding quinolines 2 in good to high yields. In the case of the electrophilic reagents, E of 2 is either I, Br, orH, depending on the reagent type, while E of 2 is H in the case of the electrophilic catalyst. 2010 American Chemical Society.
