189694-27-7Relevant articles and documents
NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines
Chen, Qian,Gao, Yang,Hu, Xiao-Qiang,Huo, Yanping,Li, Xianwei,Yang, Simin
, p. 7772 - 7779 (2021/06/30)
Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.
Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
, p. 3081 - 3089 (2020/05/08)
A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Catalyzed by Rhenium PN(H)P Complexes
Wei, Duo,Dorcet, Vincent,Darcel, Christophe,Sortais, Jean-Baptiste
, p. 3078 - 3082 (2019/01/24)
A practical and sustainable synthesis of substituted quinolines was achieved through the annulation of 2-aminobenzyl alcohol with various secondary alcohols, ketones, aldehydes, or nitriles, under hydrogen-borrowing conditions. Under the catalysis of well-defined rhenium complexes bearing tridentate diphosphinoamino ligands, the reaction proceeded efficiently (31 examples were isolated with yields up to 96 %) affording a variety of quinoline derivatives.
Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization
Cho, Chan Sik
, p. 4094 - 4097 (2007/10/03)
2-Iodoaniline reacts with terminal acetylenic carbinols in THF at 80 °C in the presence of a catalytic amount of PdCl2(PPh3) 2 and CuI along with aqueous tetrabutylammonium hydroxide to afford the corresponding 2-arylquinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial Sonogashira coupling between 2-iodoaniline and terminal acetylenic carbinols to form coupled acetylenic carbinols, isomerization of coupled acetylenic carbinols to α,β- unsaturated ketones, and cyclodehydration.
