5855-52-7Relevant academic research and scientific papers
Nickel-Catalyzed Decarbonylative Silylation, Borylation, and Amination of Arylamides via a Deamidative Reaction Pathway
Lee, Shao-Chi,Guo, Lin,Yue, Huifeng,Liao, Hsuan-Hung,Rueping, Magnus
supporting information, p. 2594 - 2598 (2017/10/31)
A nickel-catalyzed decarbonylative silylation, borylation, and amination of amides has been developed. This new methodology allows the direct interconversion of amides to arylsilanes, arylboronates, and arylamines and enables a facile route for carbon-heteroatom bond formations in a straightforward and mild fashion.
An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to β-(2-Aminophenyl)-α,β-ynones
Rode, Navnath D.,Arcadi, Antonio,Chiarini, Marco,Marinelli, Fabio
, p. 2501 - 2512 (2017/05/22)
Sequential addition/annulation reactions of sulfinate and nitrite anions to β-(2-aminophenyl)-α,β-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of β-(2-aminophenyl)-α,β-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates β-(2-aminophenyl)-α,β-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.
Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C?O and C?C Bond Activation
Yue, Huifeng,Guo, Lin,Liao, Hsuan-Hung,Cai, Yunfei,Zhu, Chen,Rueping, Magnus
supporting information, p. 4282 - 4285 (2017/04/03)
An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.
In situ generation of ammonia for the copper-catalyzed synthesis of primary aminoquinolines
Aillerie, Alexandre,Pellegrini, Sylvain,Bousquet, Till,Pélinski, Lydie
, p. 1389 - 1391 (2014/05/06)
The synthesis of primary aminoquinolines from iodoquinolines was carried out in the presence of copper(i) iodide and formamide as the solvent and source of ammonia generated in situ. The reaction proceeded under mild conditions within a few hours and was applicable to various iodoquinolines.
Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones
Coffman, Keith C.,Palazzo, Teresa A.,Hartley, Timothy P.,Fettinger, James C.,Tantillo, Dean J.,Kurth, Mark J.
, p. 2062 - 2065 (2013/06/05)
Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-,
Potent DNA-directed alkylating agents: Synthesis and biological activity of phenyl N-mustard-quinoline conjugates having a urea or hydrazinecarboxamide linker
Kakadiya, Rajesh,Dong, Huajin,Kumar, Amit,Narsinh, Dodia,Zhang, Xiuguo,Chou, Ting-Chao,Lee, Te-Chang,Shah, Anamik,Su, Tsann-Long
supporting information; experimental part, p. 2285 - 2299 (2010/06/14)
A series of N-mustard-quinoline conjugates bearing a urea or hydrazinecarboxamide linker was synthesized for antitumor evaluation. The in vitro cytotoxicity studies revealed that compounds with hydrazinecarboxamide linkers were generally more cytotoxic th
Investigation of amination in 4-chloro-2-phenylquinoline derivatives with amide solvents
Tsai, Jui-Ying,Chang, Chih-Shiang,Huang, Yi-Fan,Chen, Hua-Shin,Lin, Shao-Kai,Wong, Fung Fuh,Huang, Li-Jiau,Kuo, Sheng-Chu
supporting information; experimental part, p. 11751 - 11755 (2009/04/05)
Novel 4-amino-2-phenylquinoline derivatives were synthesized by reacting various 4-chloro-2-arylquinoline compounds having activated chloro group with the corresponding amide solvents at reflux for overnight. The activity of amination by the amide solvent
Synthetic studies using unsaturated and active phosphonium salts. A convenient preparation of furano- and pyrano[2,3-c]pyridazines and substituted quinolines
Abdou, Wafaa M.,Ganoub, Neven A.,Fahmy, Amin F.,Shaddy, Abeer M.
, p. 56 - 64 (2007/10/03)
By applying vinyl- (3) and allyltriphenyl-phosphonium bromides (9) to 4-cyano-5,6-difur-2′yl-2H-pyridazin-3-one (1) the corresponding fused 5,8-oxazolo- 6, 12 (～37%) and pyrano- 8, 13, 14 (～20%) derivatives are isolated whereas with alkylphosphonium bromides 15a,b fused furans 17a,b (22%) and isopyrroles 18a,b (～45%) are obtained. On the other hand, the reaction of 2-[(benzylidene)amino]-benzonitrile (2) with 3 and 9 yielded benzoazepines 20 and 21 (～56%). With 15a,b, quinolines 23a,b (～46%) and quinazoline 25 (～24%) are obtained.
4-Aminoquinolines as a novel class of NR1/2B subtype selective NMDA receptor antagonists
Pinard, Emmanuel,Alanine, Alexander,Bourson, Anne,Buettelmann, Bernd,Heitz, Marie-Paule,Mutel Ramanjit Gill, Vincent,Trube, Gerhard,Wyler, Rene
, p. 2615 - 2619 (2007/10/03)
Screening of the Roche compound library led to the identification of 4-aminoquinoline 4 as structurally novel NR1/2B subtype selective NMDA receptor antagonist. The SAR which was developed in this series resulted in the discovery of highly potent and in vivo active blockers.
Unprecedented outcome of base-promoted neber rearrangement of O-Mesyloxime of 2-aryl-1,2,3,4-tetrahydro-1-methylsul fonyl-4-quinolone-synthesis of 4-amino-2-arylquinolines
Mphahlele, Malose J.,Gheevarghese, Omankutty,Makhubela, Nkosinathi F.H.
, p. 303 - 314 (2007/10/03)
O-Mesyloximes derived from 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones react with sodium ethoxide in ethanol to afford the 4-amino-2-arylquinolines in high yield. No traces of the 3-amino-2-aryl-4-quinolones expected from the Neber rearrangeme
