100485-52-7Relevant academic research and scientific papers
Expedient one-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dichloroethane
Trofimov, Boris A.,Mikhaleva, Al'Bina I.,Ivanov, Andrei V.,Shcherbakova, Viktoria S.,Ushakov, Igor A.
, p. 124 - 128 (2015)
2- and 2,3-Substituted pyrroles are readily synthesized in a one-pot procedure from ketones, hydroxylamine hydrochloride, and 1,2-dichloroethane in the KOH/DMSO system (120 °C, 2-4 h), the yields of pyrroles ranging 11-85%. Aliphatic, cycloaliphatic, aromatic, and heteroaromatic ketones tolerate the reaction conditions.
Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes
Terentev, Alexander O.,Krylov, Igor B.,Vil, Vera A.,Pastukhova, Zhanna Yu.,Fastov, Sergey A.,Nikishin, Gennady I.
, p. 360 - 367 (2012)
It was found that oximes undergo deoximation in the presence of the H2O2aq-HBraq system to form ketones and bromo ketones. This reaction provided the basis for the synthesis of dibromo ketones in yields varying from 40% to 94%. This method is environmentally friendly, sustainable, and easy to perform. The results of this investigation extend the potential of the use of oximes for the protection of carbonyl group, thus offering the ability to perform not only conventional deoximation but also the subsequent bromination of ketones. The reaction is easily scaled up and dibromo ketones can be prepared in gram amounts. Versita Sp. z o.o.
Rhodium-Catalyzed C?H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides
Li, Yuan,Fang, Feifei,Zhou, Jianhui,Li, Jiyuan,Wang, Run,Liu, Hong,Zhou, Yu
, p. 3305 - 3310 (2021)
A β-hydroxy elimination instead of common oxidization to carbonyl group in secondary propargyl alcohols was successfully developed to form 2-benzyl substituted isoquinoline N-oxides by a Rhodium-catalyzed C?H activation and annulation cascade, in which moderate to excellent yields (up to 92%) could be obtained under mild reaction conditions, along with good regioselectivity, broad generality and applicability. (Figure presented.).
Synthesis, Structure, and Photochemical Behavior of [5]Heli-viologen Isomers
Zhang, Xiaoping,Clennan, Edward L.,Arulsamy, Navamoney,Weber, Rachael,Weber, Jacob
, p. 5474 - 5486 (2016)
The syntheses of isomeric helical viologens that have potential applications in supramolecular chemistry and catalysis have been developed. The structures of the molecules and their solid-state packing motifs have been determined by X-ray crystallography. Computational studies demonstrate that the magnitude of their racemization barriers is primarily determined by the identity of the helical scaffold and is insensitive to the placement of the viologen functional group. The isomers are similar in their photophysical behavior but very different in their photochemical behavior.
A facile and practical synthesis of N-acetyl enamides
Tang, Wenjun,Capacci, Andrew,Sarvestani, Max,Wei, Xudong,Yee, Nathan K.,Senanayake, Chris H.
, p. 9528 - 9530 (2009)
(Chemical Equation Presented) A facile and practical method for the synthesis of N-acetyl α-arylenamides has been developed from corresponding ketoximes as the starting materials with ferrous acetate as the reducing reagent. This methodology offers mild reaction conditions, simple purification procedures, and high yields for a variety of N-acetyl enamides.
Nitrimines as reagents for metal-free formal C(sp2)-C(sp2) cross-coupling reactions
Angeles-Dunham, Veronica V.,Nickerson, David M.,Ray, Devin M.,Mattson, Anita E.
, p. 14538 - 14541 (2014)
Nitrimines are employed as powerful reagents for metal-free formal C(sp2)-C(sp2) cross-coupling reactions. The new chemical process is tolerant of a wide array of nitrimine and heterocyclic coupling partners giving rise to the corresponding di- or trisubstituted alkenes, typically in high yield and with high stereoselectivity. This method is ideal for the metal-free construction of heterocycle-containing drug targets, such as phenprocoumon.
Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines
Wang, Quannan,Lou, Jiang,Huang, Zilong,Yu, Zhengkun
, p. 2083 - 2092 (2019)
Rhodium(III)-catalyzed annulation of acetophenone O-acetyl oximes with allenoates was achieved, affording isoquinolines in good to excellent yields with high regioselectivities under redox-neutral conditions. Allenoates acted as the C2 synthons in the annulation reaction. The present synthetic methodology features good functional group tolerance and avoids metal salts as the external oxidants. The proposed mechanism suggests that the reaction proceeds through arene C-H activation, allene insertion, and C-N coupling.
Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters
Liu, Jiechun,Lin, Haojiang,Jiang, Huanfeng,Huang, Liangbin
supporting information, p. 484 - 489 (2022/01/20)
Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.
Visible-light-promoted olefinic trifluoromethylation of enamides with CF3SO2Na
Tang, Kai,Chen, Yixuan,Guan, Jianping,Wang, Zhujun,Chen, Kai,Xiang, Haoyue,Yang, Hua
supporting information, p. 7475 - 7479 (2021/09/08)
A visible-light-promoted olefinic C-H trifluoromethylation of enamides was developed by employing cheap and stable Langlois’ reagent as the CF3source. A series of β-CF3enamides were obtained in moderate to good yields with highE-isomer selectivity under mild conditions. Preliminary mechanistic studies suggest that molecular oxygen acts as the terminal oxidant for this net oxidative process, and theEisomer selectivity could be well explained by a base-assisted deprotonation of the cation intermediate.
Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds
Chang, Junbiao,Deng, Wei-Qiao,Kong, Lingheng,Li, Xingwei,Liu, Bingxian,Sun, Lincong,Wang, Fen,Zhao, Yanlian
supporting information, p. 8268 - 8271 (2021/08/25)
Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is
