65745-74-6Relevant academic research and scientific papers
Visible light-induced one-pot synthesis of CF3/CF2-substituted cyclobutene derivatives
Ding, Aishun,Guo, Hao,Hu, Xiao,Xu, Dawen
supporting information, p. 7441 - 7444 (2021/08/03)
An efficient one-pot approach for the controllable synthesis of trifluoromethyl/gem-difluoromethylene substituted cyclobutene derivatives has been developed. The mechanism may involve visible light-induced [2+2]-cycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by base-promoted dehydrobromination, [1,3]-H shift and further dehydrofluorination. A variety of CF3/CF2-substituted cyclobutenes that are currently difficult to obtain are afforded in good yields in this protocol, which may find its way into future fluorinated cyclobutene preparation.
Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles
Zhou, Meimei,Yu, Keyang,Liu, Jianxin,Shi, Weimei,Pan, Yingming,Tang, Haitao,Peng, Xiangjun,Liu, Qian,Wang, Hengshan
, p. 16246 - 16251 (2021/05/19)
Selective C1-H/C4-H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two diff
Identification of N-acyl quinolin-2(1H)-ones as new selective agents against clinical isolates of Acanthamoeba keratitis
Abad-Grillo, Teresa,Lorenzo-Morales, Jacob,McNaughton-Smith, Grant,Freijo, Mónica Blanco,López-Arencibia, Atteneri,Pi?ero, José E.,Reyes-Batlle, María
, (2020/04/08)
A collection of N-substituted quinolin-2(1H)-ones were screened against a panel of clinically relevant protozoa (Leishmania, Trypanosoma and Acanthamoeba). Three quinolin-2(1H)-one compounds were identified as selective anti-Acanthamoeba agents. Further assessment revealed that these compounds were active against both trophozoite and cyst forms of A. castellanii Neff, and caused protozoa death via apoptosis. The data presented herein identify N-acyl quinolin-2(1H)-ones as a promising new class of selective anti-Acanthamoeba agents.
Base-promoted aerobic oxidation of: N -alkyl iminium salts derived from isoquinolines and related heterocycles
Bai, Li-Gang,Zhou, Yue,Zhuang, Xin,Zhang, Liang,Xue, Jian,Lin, Xiao-Long,Cai, Tian,Luo, Qun-Li
, p. 197 - 203 (2020/01/13)
Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.
Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors
Guo, Yafei,Harutyunyan, Syuzanna R.
supporting information, p. 12950 - 12954 (2019/08/07)
General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.
Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones
Mishra, Abhishek Kumar,Morgon, Nelson Henrique,Sanyal, Suparna,Robinson de Souza, Aguinaldo,Biswas, Srijit
, p. 3930 - 3939 (2018/09/14)
The present study reports the synthesis of N-alkylated pyridones and benzothiazolones via O- to N-alkyl group migration under transition metal-free TfOH-catalyzed reaction conditions for the first time, to the best of our knowledge. Primary as well as secondary alkyl groups smoothly migrate under the present reaction conditions. Moreover, a minor modification of the protocol used in this study is found to be applicable for an entirely new tandem synthesis of 2-alkoxy-N-heterocycles from the simplest starting materials in a solvent-free reaction conditions. Density Functional Theory (DFT) calculation identifies the energy species associated with the rearrangement, whereas, mechanistic experiments explore the role of the catalyst as the alkyl group transfer mediator. (Figure presented.).
An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions
Motaleb, Abdul,Bera, Asish,Maity, Pradip
, p. 5081 - 5085 (2018/07/29)
A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.
Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
Feng, Bin,Li, Yang,Li, Huan,Zhang, Xu,Xie, Huamei,Cao, Hongen,Yu, Lei,Xu, Qing
, p. 6769 - 6775 (2018/05/29)
A specific N-alkylation of 2-hydroxypyridines is achieved by reacting with organohalides under catalyst- and base-free conditions. The observed HX-facilitated conversion of pyridyl ether intermediates to 2-pyridone products may account for the success and
Iodine-catalyzed oxidative multiple C-H bond functionalization of isoquinolines with methylarenes: An efficient synthesis of isoquinoline-1,3,4(2: H)-triones
Zhu, Di,Luo, Wen-Kun,Yang, Luo,Ma, Da-You
supporting information, p. 7112 - 7116 (2017/09/07)
An iodine-catalyzed multiple C-H bond functionalization of isoquinolines with methylarenes via a successive benzylic sp3 C-H iodination/N-benzylation/amidation/double sp2 C-H oxidation sequence is developed. This reaction utilizes un
Copper-Mediated Oxidative Functionalization of C(sp3)-H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones
Wang, Dingyi,Zhang, Rongxing,Deng, Ruihong,Lin, Sen,Guo, Shengmei,Yan, Zhaohua
, p. 11162 - 11167 (2016/11/28)
A copper-mediated oxidative functionalization of C(sp3)-H bonds with isoquinolines via a radical process without ligands was achieved. The present system exhibits a novel pathway for the preparation of N-alkyl (benzyl) isoquinolin-1(2H)-ones in moderate to high yields. In addition, this procedure provides a simple method to afford 5-oxaprotoberberinones and their derivatives in two steps.
