- Water mediated procedure for preparation of stereoselective oximes as inhibitors of MRCK kinase
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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.
- Luqman, Suaib,Misra, Krishna,Pandey, Jyoti,Shrivash, Manoj Kumar,Shukla, Akhilesh Kumar,Singh, Shilipi
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- A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system
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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.
- Jiang, Xiaoying,Xu, Xiaohe,Lin, Yuyan,Yan, Yiyan,Li, Pingping,Bai, Renren,Xie, Yuanyuan
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supporting information
p. 5879 - 5885
(2018/09/06)
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- Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts
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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.
- Hyodo, Kengo,Togashi, Kosuke,Oishi, Naoki,Hasegawa, Genna,Uchida, Kingo
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supporting information
p. 5788 - 5793
(2016/11/06)
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- 3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water
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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.
- Yu, Jiatao,Jin, Yong,Lu, Ming
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supporting information
p. 1175 - 1180
(2015/04/22)
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- Substituted Acyloxyamidines as HCV NS3/4A Inhibitors
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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.
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Paragraph 0150; 0151
(2015/05/26)
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- A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes
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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.
- Yu, Jiatao,Cao, Xiaohua,Lu, Ming
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supporting information
p. 5751 - 5755
(2015/02/02)
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- One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers
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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.
- Liu, Cuibo,Yin, Xuguang,Chang, Jing,Tang, Xiangyang,Zhang, Bin
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p. 101 - 108
(2014/08/18)
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- Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
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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).
- Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
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experimental part
p. 308 - 311
(2012/08/28)
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- Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction
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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
- Chen, Wei,Yu, Wei-Guo,Shi, Hai-Bo,Lu, Xiao-Yan
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p. 308 - 311
(2015/03/04)
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- Electrochemical tandem synthesis of oximes from alcohols using KNO 3 as the nitrogen source, mediated by tin microspheres in aqueous medium
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Electrochemical oximation of alcohols was realized with KNO3 as the nitrogen source mediated by tin microspheres.
- Zhang, Li,Chen, He,Zha, Zhenggen,Wang, Zhiyong
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supporting information; experimental part
p. 6574 - 6576
(2012/07/30)
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- Simple, efficient and green synthesis of oximes under ultrasound irradiation
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The condensation of aldehydes andketones with hydroxylamine hydrochloride gives oximes in 81-95%yields in water andEtOH under ultrasound irradiation. Compared to conventional methods, the main advantages of the present procedure are milder reaction conditions, shorter reaction times and higher yields.
- Khoramabadi-Zad,Azadmanesh,Rezaee
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p. 192 - 194
(2013/01/09)
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- AlPW12O40 and AlPMo12O40 as highly effective and eco-friendly catalysts for aldoximation of aldehydes under solvent-free conditions
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The oxime formation of aromatic aldehydes has directly been carried out with hydroxylamine hydrochloride using heteropoly acids (AlPW12O 40, AlPMo12O40) as catalysts in the absence of solvent. It is found that these heteropoly acids were effective catalysts for the formation of oxime of aldehydes. This method consistently has the advantage of high yields of the products, short reaction time, mild and solvent-free conditions, cleaner reactions and isolation procedures.
- Fazaeli, Razieh,Aliyan, Hamid
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experimental part
p. 855 - 858
(2012/04/04)
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- Alumina sulfuric acid mediated solvent-free and one-step Beckmann rearrangement of ketones and aldehydes and a useful reagent for synthesis of keto- and ald-oximes
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Under solvent-free conditions, one-step Beckmann rearrangement of a variety of ketones and aldehydes could proceed in the presence of alumina sulfuric acid (ASA). The ASA reagent can also be used for the preparation of keto- and ald-oximes.
- Hosseini-Sarvari, Mona,Sharghi, Hashem
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p. 205 - 208
(2007/10/03)
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- Titanium oxide (TiO2) catalysed one-step Beckmann rearrangement of aldehydes and ketones in solvent free conditions
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In the presence of titanium oxide (TiO2) and without any additional organic solvents, Beckmann rearrangement of several ketones and aldehydes was performed in good yield.
- Sharghi, Hashem,Hosseini Sarvari, Mona
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p. 176 - 178
(2007/10/03)
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- Solvent-free and one-step Beckmann rearrangement of ketones and aldehydes by zinc oxide
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In the presence of zinc oxide and without any additional organic solvents, Beckmann rearrangement of several ketones and aldehydes were performed in good yields.
- Sharghi, Hashem,Hosseini, Mona
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p. 1057 - 1060
(2007/10/03)
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- Selective synthesis of E and Z isomers of oximes
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The highly stereoselective conversion of aldehydes and ketones to their corresponding oximes with hydroxylamin hydrochloride are catalyzed by CuSO4 and K2CO3. This method occurs under mild reaction conditions with high yields.
- Sharghi,Sarvari
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- One-step Beckmann rearrangement from carbonyl compounds and hydroxylamine hydrochloride in Al2O3/CH3SO3H (AMA) as a new reagent
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A facile and efficient synthetic procedure, for one-step Beckmann rearrangement of aldehydes and ketones with hydroxylamine hydrochloride and Al2O3/CH3SO3H (AMA) has been developed; cyclohexanone has been converted into ε-caprolactam in a quantitative yield.
- Sharghi,Sarvari
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p. 446 - 449
(2007/10/03)
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- Ceric ammonium nitrate oxidation of aldoximes in aliphatic nitriles as solvents: A new way for synthesis of 1,2,4-oxadiazoles
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Oxidation of aromatic aldoximes with one-electron oxidant ceric ammonium nitrate CAN in acetonitrile and propionitrile, has been investigated. Aromatic nitrile oxides, formed in situ, underwent 1,3-cycloaddition with aliphatic nitriles and 5-alkyl-3-aryl-1,2,4-oxadiazoles are produced in moderate to high yields. The mechanism of the reaction based on the transformations of intermediate aldazine di-N-oxides is discussed.
- Giurg,Mlochowski
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p. 1093 - 1101
(2007/10/03)
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- Synthesis and Biological Activity of Benzaldehyde O-Alkyloximes as Abscisic Acid Mimics (Part 1)
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Twenty-four benzaldehyde O-alkyloximes having a carboxylic moiety at the α-position of the oxime-oxygen were prepared as abscisic acid (ABA) mimics.Their effects on some physiological and biochemical processes of selected plant species were investigated in comparison to those of ABA.The mimics exhibited ABA-like activity by inhibiting germination and α-amylase induction.They also induced stomatal closure coupled with a reduction in transpiration.
- Yoshikawa, Hiromichi,Fujimoto, Eri,Doi, Keiko
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p. 256 - 260
(2007/10/02)
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- 1H and 13C NMR Studies of some O-Carbamoyloximes
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The 1H and 13C NMR spectra were assigned for a series of O-carbamoyloximes of ortho- and para-substituted benzaldehyde.These compounds exist exclusively in the E configuration.The aromatic protons and carbons show correlations with the appropriate substituent-induced shifts and with Hammett parameters. KEY WORDS O-Carbamoyloximes 1H and 13C NMR Hammett parameters
- Wazeer, Mohammed I. M.,Ali, Sk. A.,Arab, Mohammed
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p. 1102 - 1104
(2007/10/02)
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- Herbicidal 3-isoxazolidinones and hydroxamic acids
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Novel 3-isoxazolidinone compounds and novel hydroxamic acid intermediates from which they are prepared exhibit herbicidal activity to grassy and broad-leaf plant species while leaving legumes, especially soybeans, unaffected. The preparation and herbicidal activity of the compounds is exemplified.
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- Herbicidal isoxazolidine-3,5-diones
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2-Substituted isoxazolidine-3,5-diones and isoxazolidine-3-one-5-thiones exhibit herbicidal activity, controlling effectively the growth of a wide spectrum of grassy and broad-leaved plant species. The preparation and herbicidal activity of the compounds is exemplified.
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