27356-52-1Relevant articles and documents
Ruthenium-catalyzed synthesis of quinolines from anilines and allylammonium chlorides in an aqueous medium via amine exchange reaction
Cho, Chan Sik,Kim, Joon Seok,Oh, Byoung Ho,Kim, Tae-Jeong,Shim, Sang Chul,Yoon, Nam Sik
, p. 7747 - 7750 (2000)
Anilines react with allylammonium chlorides in an aqueous medium (H2O-dioxane) in the presence of a catalytic amount of RuCl2(PPh3)3 together with SnCl2·2H2O to give the corresponding quinolines in moderate to good yields. The existence of SnCl2·2H2O is necessary for the effective formation of quinolines, and a reaction pathway involving amine exchange reaction between anilines and allylammonium chlorides to form an imine is proposed for this catalytic process. (C) 2000 Elsevier Science Ltd.
Oxygen-implanted MoS2 nanosheets promoting quinoline synthesis from nitroarenes and aliphatic alcohols via an integrated oxidation transfer hydrogenation-cyclization mechanism
Gao, Zhuyan,Huang, Zhipeng,Lu, Jianmin,Mu, Junju,Ren, Puning,Su, Kaiyi,Wang, Feng,Zhang, Chaofeng,Zhang, Shichao
, p. 1704 - 1713 (2022/03/08)
We herein report that MoS2 with oxygen-implanting modification (O-MoS2) can work as a multifunctional catalyst to achieve the one-pot quinoline synthesis from basic nitroarenes and aliphatic alcohols. Different from common knowledge that the application of MoS2-based catalysts and above quinoline synthesis need anaerobic conditions, we conduct the heterogeneous catalysis under an unusual air atmosphere. Catalyst characterization and experimental results indicate that the MoOx clusters implanted in the MoS2 skeleton, not the coordinatively unsaturated Mo sites (CUS Mo), dominate the generation of quinolines. By overturning the catalysis perception that O2 adsorption on MoSx can deactivate the MoS2-based catalysts using an efficient method for in situ healing of the MoOx structure in O-MoS2 and protecting the O-MoS2 catalyst by inhibiting unwanted MoOx elimination with extra H*, we innovatively introduce O2 into the quinoline synthesis. The robust O-MoS2 can be consecutively used ten times without regeneration and it offers 69-75% yields of 2-methylquinoline from nitrobenzene and ethanol. Furthermore, different from the traditional transfer hydrogenation-condensation mechanism, an integrated oxidation-transfer hydrogenation-cyclization mechanism is proposed over the O-MoS2 catalyst.
One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
Makhmutov
, p. 1166 - 1172 (2018/10/24)
One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
