58022-21-2Relevant academic research and scientific papers
Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
supporting information, p. 3735 - 3742 (2021/05/04)
Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
Metal-, Photocatalyst-, and Light-Free Minisci C-H Acetylation of N-Heteroarenes with Vinyl Ethers
Dong, Jianyang,Liu, Jianhua,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 4374 - 4378 (2021/06/21)
Herein, we report a mild, operationally simple method for Minisci C-H acetylation of N-heteroarenes using vinyl ethers as robust, inexpensive acetyl sources. The reactions do not require a conventional photocatalysis, electrocatalysis, metal catalysis, light activation, or high temperature. This method is thus significantly more sustainable than previously reported methods in terms of cost, reagent toxicity, and waste generation. This protocol can be expected to obtain medically relevant molecules from abundant feedstock materials.
Carbonylative Acetylation of Heterocycles
Zhang, Youcan,Yin, Zhiping,Wu, Xiao-Feng
supporting information, p. 213 - 216 (2020/01/22)
Herein, a new procedure for the carbonylative acetylation of heterocycles has been developed. In this process, organic peroxide acts as the methyl source. Various heterocycles were transformed into the corresponding methyl heterocyclic ketones in moderate to good yields.
Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids
Wang, Xiu-Zhi,Zeng, Cheng-Chu
supporting information, p. 1425 - 1430 (2019/02/01)
An efficient and mild protocol has been developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids. Distinct from the conventional Minisci acylation conditions, the chemistry was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt, as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. Scale-up experiment also demonstrates the practicality of the approach.
Iron-Catalyzed Minisci Type Acetylation of N-Heteroarenes Mediated by CH(OEt)3/TBHP
Srinivasulu,Shantharjun,Vani,Ashalu, K. Chinna,Mohd,Wencel-Delord,Colobert,Reddy, K. Rajender
supporting information, p. 1815 - 1819 (2019/02/20)
Iron-catalyzed acetylation of electron deficient N-heteroarenes has been reported using triethylorthoformate as robust and inexpensive acetyl source. This new method is successfully applied for the acetylation of quinolines, isoquinoline, quinoxalines, arylpyridines, bipyridines, and benzothiazole.
Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
Jia, Wei,Jian, Yong,Huang, Binbin,Yang, Chao,Xia, Wujiong
supporting information, p. 1881 - 1886 (2018/08/28)
A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly
Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
Galloway, Jordan D.,Mai, Duy N.,Baxter, Ryan D.
supporting information, p. 5772 - 5775 (2017/11/10)
A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.
Metal-free decarboxylative acylation of isoquinolines using α-keto acids in water
Chaubey, Narendra R.,Singh, Krishna Nand
supporting information, p. 2347 - 2350 (2017/05/29)
An efficient method for acylation of isoquinolines has been developed using α-ketoacids under metal- and additive-free conditions in water. The protocol involves C(sp2)–H functionalization of isoquinolines providing an easy access to C1-benzoylated isoquinolines, which constitute the core structure of a number of biological active compounds and serve as key intermediate in the synthesis of many alkaloids.
X-ray structural and biological evaluation of a series of potent and highly selective inhibitors of human coronavirus papain-like proteases
Báez-Santos, Yahira M.,Barraza, Scott J.,Wilson, Michael W.,Agius, Michael P.,Mielech, Anna M.,Davis, Nicole M.,Baker, Susan C.,Larsen, Scott D.,Mesecar, Andrew D.
, p. 2393 - 2412 (2014/04/17)
Structure-guided design was used to generate a series of noncovalent inhibitors with nanomolar potency against the papain-like protease (PLpro) from the SARS coronavirus (CoV). A number of inhibitors exhibit antiviral activity against SARS-CoV infected Ve
Synthesis of 1-acylisoquinolines from isoquinoline, alcohols, and CCl 4 catalyzed by iron complexes
Khusnutdinov,Baiguzina,Mukminov
experimental part, p. 1399 - 1402 (2011/01/04)
Reactions of isoquinoline with normal alcohols (ethanol, 1-propanol, 1-butanol) and tetrachloromethane in the presence of iron-containing catalysts afforded 1-acylisoquinolines in 38-75% yield.
