3717-27-9Relevant academic research and scientific papers
Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
, p. 308 - 311 (2012)
A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yie
Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase
Luqman, Suaib,Misra, Krishna,Pandey, Jyoti,Shrivash, Manoj Kumar,Shukla, Akhilesh Kumar,Singh, Shilipi
, (2020/07/08)
Stereoselective aldoximes, preferably Z form have been obtained from α-cyano substituted carbonyl conjugated alkenes. This reaction occurs through Michael addition type reaction followed by retro-Knoevenagel reaction without transition-metal catalysis via C–C bond cleavage. These oximes are evaluated against cancer cell lines employing mechanistic study. Two oximes showed significant cytotoxic activity, which through in silico studies were found to inhibit MRCK Kinase, responsible for metastatic spread of cancer mortality.
A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
supporting information, p. 5879 - 5885 (2018/09/06)
An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.
Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts
Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo
supporting information, p. 5788 - 5793 (2016/11/06)
The transoximation reaction enables the transfer of an oxime to a carbonyl compound and is catalyzed by transoximase in the pupae of the silkworm. Inspired by this bio-synthetic pathway, we achieved the transoximation of oximes to aldehydes and ketones catalyzed by a Br?nsted acid under mild conditions. Hydroxylamine salt, which necessitates a stoichiometric amount of base, was not required. NMR analysis clarified that this reaction proceeded through hydroxylamines generated by the successive hydrolysis of the oxime in situ. In addition, an environmentally benign method for catalytic transoximation was demonstrated in aqueous medium on a one hundred gram scale and the reaction filtrate containing the catalyst was recovered and reused over 10 times.
3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water
Yu, Jiatao,Jin, Yong,Lu, Ming
supporting information, p. 1175 - 1180 (2015/04/22)
A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.
Substituted Acyloxyamidines as HCV NS3/4A Inhibitors
-
Paragraph 0150; 0151, (2015/05/26)
Disclosed herein is a compound of Formula I or a pharmaceutically acceptable salt thereof, in which A, G, R1 and R2 are as defined herein. The compounds and pharmaceutical compositions of the compounds are suitable for the treatment of HCV infection in mammals and are also useful to modulate or inhibit NS3/4 dimerization.
A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes
Yu, Jiatao,Cao, Xiaohua,Lu, Ming
supporting information, p. 5751 - 5755 (2015/02/02)
A simple and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to corresponding oximes by using toluene as the solvent is described. This practical method can use O2 as the economic and green oxidant, tolerate a wide range of substrates, which can afford the target oximes in moderate to excellent yields.
One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers
Liu, Cuibo,Yin, Xuguang,Chang, Jing,Tang, Xiangyang,Zhang, Bin
, p. 101 - 108 (2014/08/18)
A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective CF bond cleavage.
Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
experimental part, p. 308 - 311 (2012/08/28)
A highly stereoselective synthesis of E-isomer of aldoximes was developed through a basecatalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95 : 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).
Electrochemical tandem synthesis of oximes from alcohols using KNO 3 as the nitrogen source, mediated by tin microspheres in aqueous medium
Zhang, Li,Chen, He,Zha, Zhenggen,Wang, Zhiyong
supporting information; experimental part, p. 6574 - 6576 (2012/07/30)
Electrochemical oximation of alcohols was realized with KNO3 as the nitrogen source mediated by tin microspheres.
