835-38-1Relevant articles and documents
Synthesis of functionalised 2,3-dihydroquinolin-4(1: H)-ones vs. quinoline or N -alkenylindole derivatives through sequential reactions of 2-alkynylanilines with ketones
Marsicano, Vincenzo,Arcadi, Antonio,Chiarini, Marco,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia
, p. 421 - 438 (2021/01/29)
This study describes diversity-oriented synthesis of 2,2,3-substituted-2,3-dihydroquinolin-4(1H)-ones vs. functionalised quinoline or N-alkenylindole derivatives through Br?nsted acid mediated or Lewis acid catalyzed sequential reactions of 2-alkynylanilines with ketones. In particular, a series of challenging quinolin-4-one derivatives are prepared with good functional group tolerance in an atom-economical fashion by using p-toluenesulfonic acid monohydrate as a promoter of the reaction of ketones with 2-alkynylanilines in EtOH at reflux, while the same starting materials give the corresponding 4-substituted quinolines in toluene at 110 °C both in the presence of p-toluenesulfonic acid monohydrate as the promoter and FeCl3 as the catalyst. The divergent formation of N-alkenylindole derivatives occurs by switching to the use of ZnBr2 as the catalyst under the same reaction conditions. Conversely, only 4-methylsubstituted quinoline derivatives were isolated by reacting 2-ethynylanilines and/or 2-trimethylsylilanilines with ketones in all examined cases. This journal is
Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks
Li, Liping,Gao, Hui,Sun, Ming,Zhou, Zhi,Yi, Wei
supporting information, p. 5473 - 5478 (2020/07/14)
Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.
A Reusable MOF-Supported Single-Site Zinc(II) Catalyst for Efficient Intramolecular Hydroamination of o-Alkynylanilines
Li, Beibei,Ju, Zhanfeng,Zhou, Mi,Su, Kongzhao,Yuan, Daqiang
supporting information, p. 7687 - 7691 (2019/05/15)
The exploitation of new and active earth-abundant metal catalysts is critical for sustainable chemical production. Herein, we demonstrate the design of highly efficient, robust, and reusable ZnII-bipyridine-based metal–organic framework (MOF) catalysts for the intramolecular hydroamination of o-alkynylanilines to indoles. Under similar conditions homogeneous catalytic systems mainly provide hydrolysate. Our results prove that MOFs support unique internal environments that can affect the direction of chemical reactions. The ZnII-catalyzed hydroamination reaction can be conducted without additional ligands, base, or acid, and is thus a very clean reaction system with regard to its environmental impact.