393109-89-2Relevant articles and documents
Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines
Hu, Yan,Nan, Jiang,Yin, Jiacheng,Huang, Guanjie,Ren, Xin,Ma, Yangmin
supporting information, p. 8527 - 8532 (2021/11/13)
Here we report a novel Rh-catalyzed C-H/C-H alkenylation of N-arylmethanimines with vinylene carbonate acting as a vinylene unit. Forty examples of C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, a lower loading of catalyst, and the capacity for postfunctionalization with bioactive molecules.
Facile synthesis of substituted quinolines by iron(iii)-catalyzed cascade reaction between anilines, aldehydes and nitroalkanes
Mahato, Sachinta,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Majee, Adinath
, p. 7907 - 7917 (2019/09/06)
A library of substituted quinolines has been synthesized by the reaction of aldehydes, anilines and nitroalkanes using a catalytic amount of Fe(iii) chloride. The reaction is a simple, efficient, one-pot, three-component domino strategy in ambient air which afforded the products in high yields. A probable pathway of the reaction is a sequential aza-Henry reaction/cyclization/denitration. The use of commercially available chemicals as starting materials, an inexpensive metal catalyst, aerobic reaction conditions, tolerance of a wide range of functional groups, and operational simplicity are the notable advantages of this present protocol.
Molybdenum-Catalyzed Sustainable Friedl?nder Synthesis of Quinolines
Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Sanz, Roberto
supporting information, p. 2216 - 2220 (2018/06/14)
Polysubstituted quinolines have been efficiently synthesized from nitroarenes and glycols, as reducing agents, under dioxomolybdenum(VI)-catalysis. Interestingly, the waste reduction byproduct is incorporated into the final heterocycle. This method repres
Palladium-catalyzed synthesis of quinolines from allyl alcohols and anilines
Xu, Jingxiu,Sun, Jing,Zhao, Jinwu,Huang, Bin,Li, Xiaohan,Sun, Yulun
, p. 36242 - 36245 (2017/08/02)
A process for quinoline synthesis through palladium-catalyzed oxidative cyclization of aryl allyl alcohols and anilines is described. This process works in the absence of acid, base and any other additive and has a broad substrate scope, tolerating electron-withdrawing groups such as nitryl, trifluoromethyl and so on. A series of quinolines are prepared in satisfactory yields.
Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
Li, Chunsheng,Li, Jianxiao,An, Yanni,Peng, Jianwen,Wu, Wanqing,Jiang, Huanfeng
, p. 12189 - 12196 (2016/12/23)
An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.
An Unexpected Construction of 2-Arylquinolines from N-Cinnamylanilines through sp3 Ci-H Aerobic Oxidation Induced by a Catalytic Radical Cation Salt
Liu, Fang,Yu, Liangliang,Lv, Shiwei,Yao, Junjun,Liu, Jing,Jia, Xiaodong
supporting information, p. 459 - 465 (2016/02/12)
An unexpected reaction of cinnamylanilines was achieved through the radical cation salt-induced aerobic oxidation of sp3 C-H bonds, providing a series of 2-arylquinolines. The mechanistic study shows that the cinnamylaniline was oxidized to an imine, which was attacked by the aniline generated through decomposition of the corresponding imine. After further intramolecular cyclization and aromatization, 2-arylquinolines were obtained. This reaction provides a new method to construct 2-arylquinolines from readily accessible starting materials.
Catalytic arylation of a C-H bond in pyridine and related six-membered N-heteroarenes using organozinc reagents
Hyodo, Isao,Tobisu, Mamoru,Chatani, Naoto
supporting information; experimental part, p. 1357 - 1365 (2012/08/08)
Despite significant advances in the catalytic direct arylation of heteroarenes, the application of this reaction to pyridines has been met with limited success. An oxidative nucleophilic arylation strategy has been developed to overcome this problem. Pyridine, pyrazine, quinolone, and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using the developed nickel-catalyzed reaction. This protocol serves as a complementary method to catalytic direct arylation reactions. Less is more: Pyridine, pyrazine, quinoline and related electron-deficient N-heteroarenes can be arylated at the most electrophilic site using organozinc reagents through nickel catalysis. This protocol serves as a complementary method to catalytic direct arylation reactions. Copyright
Synthesis of substituted pyridines and quinolines
Hill, Matthew D.,Movassaghi, Mohammad
, p. 1115 - 1119 (2008/02/02)
A variety of N-vinyl and N-aryl amides were converted to the corresponding pyridine and quinoline derivatives, respectively. Amide activation and nucleophilic addition of copper(I) (trimethylsilyl)acetylide efficiently provided the desired alkynyl imines. Ruthenium-catalyzed protodesilylation and cycloisomerization of these imines gave the corresponding azaheterocycles. Georg Thieme Verlag Stuttgart.
Synthesis of substituted pyridine derivatives via the ruthenium-catalyzed cycloisomerization of 3-azadienynes
Movassaghi, Mohammad,Hill, Matthew D.
, p. 4592 - 4593 (2007/10/03)
We describe a two-step conversion of various N-vinyl and N-aryl amides to the corresponding substituted pyridines and quinolines, respectively. The process involves the direct conversion of amides, including sensitive N-vinyl amides, to the corresponding trimethylsilyl alkynyl imines followed by a ruthenium-catalyzed protodesilylation and cycloisomerization. A wide range of new alkynyl imines are prepared and readily converted to the corresponding azaheterocycles. Copyright
Imino-Diels-Alder and imino-aldol reactions catalyzed by samarium diiodide
Collin, Jacqueline,Jaber, Nada,Lannou, Marie Isabelle
, p. 7405 - 7407 (2007/10/03)
In the presence of a catalytic amount of samarium diiodide in methylene chloride, aromatic imines react with Danishefsky diene to form tetrahydropyridine-4-ones in high yields. Under the same conditions, various imino-aldol reactions afford β-amino esters or β-amino ketones.
