cas 13372-81-1, CINNAMALDEHYDE OXIME | Articles data

Articles about 13372-81-1Total 58 be found

Article title
Article abstract
Author
Journal number and time
Download

A rapid and efficient solvent-free microwave-assisted synthesis of pyrazolone derivatives containing substituted isoxazole ring
An efficient synthesis of 4-substituted pyrazolone derivatives was developed. 4-Substituted pyrazolone derivatives were synthesized in 78-97% yields starting from various 3-substituted isoxazole-5-carbaldehydes, ethyl acetoacetate and hydrazine under micr
Zhang, Dawei,Zhang, Yumin,Zhao, Tianqi,Li, Jing,Hou, Yaya,Gu, Qiang
p. 2979 - 2987
(2016)
Read Online

Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity
Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect
Feng, Qiang,Huang, Hai,Sun, Jianwei
supporting information
p. 2431 - 2436
(2021/05/05)

Site selective synthesis and anti-inflammatory evaluation of Spiro-isoxazoline stitched adducts of arteannuin B
A library of new spiroisoxazoline analogues of arteannuin B was synthesized through 1, 3-dipolar cycloaddition in stereoselective fashion and consequently screened for anti-inflammatory activity in RAW 264.7 macrophage cells. Three potent analogues (8i, 8 m, and 8n) were found to attenuate the LPS induced release of cytokines IL-6 and TNF-α more potently than the parent molecule. Also, the inhibition of LPS induced nitric oxide production in these cells show moderate to high efficacy. None of the three potent molecules have altered the viability of RAW 264.7 cells following 48 h incubation suggesting that the inhibition of cytokines and nitric oxide production exhibited in the cells was not due to toxicity. In addition, these compounds exhibit an IC50 range of 0.17 μM-1.57 μM and 0.09 μM-0.35 μM for the inhibition of IL-6 release and nitric oxide production respectively. The results disclose potent inhibition of pro-inflammatory mediators which are encouraging and warrant further investigations to develop new therapeutic agents for inflammatory diseases.
Ur Rasool, Javeed,Sawhney, Gifty,Shaikh, Majeed,Nalli, Yedukondalu,Madishetti, Sreedhar,Ahmed, Zabeer,Ali, Asif
(2021/10/16)

A Synergic Activity of Urea/Butyl Imidazolium Ionic Liquid Supported on UiO-66-NH2 Metal–Organic Framework for Synthesis of Oximes
An efficient supported ionic liquid catalyst is designed for condensation reaction of aldehydes and ketones. The Zr-based metal–organic framework (MOF), UiO-66-NH2, was initially functionalized with N,N′-dibutyl imidazolium ionic liquid (UiO-66-NH2-ILBr–), and then urea was attached to the ionic liquid (IL) to form a task-specific IL. Bromide was exchanged with tetrafluoroborate and the catalyst exhibits excellent performance for the synthesis of oximes. The ionic liquid/urea coupling showed a synergistic effect on the efficiency of the reaction. The supported catalyst system was recycled simply by filtration and reused for five times without significant decrease in its activity. The catalyst was characterized with PXRD, FTIR, TGA, XPS, BET, FE-SEM, EDS, elemental mapping and elemental analysis (CHN). Graphic Abstract: MOF/IL/urea catalytic system was used for the synthesis of oximes[Figure not available: see fulltext.].
Askari, Saeed,Jafarzadeh, Mohammad,Christensen, David Benjamin,Kegn?s, S?ren
p. 3159 - 3173
(2020/04/21)

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles
Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.
Xu, Jiaxi,Gao, Yu,Li, Zhenjiang,Liu, Jingjing,Guo, Tianfo,Zhang, Lei,Wang, Haixin,Zhang, Zhihao,Guo, Kai
p. 311 - 315
(2020/01/25)

Design, synthesis and evaluation of novel levoglucosenone derivatives as promising anticancer agents
A series of levoglucosenone-derived 1,2,3-triazoles and isoxazoles featuring a flexible spacer between the heteroaromatic and anhydropyranose cores have been designed and synthesized following an hetero Michael // 1,3-dipolar cycloaddition path. The use o
Borini Etichetti, Carla M.,Cicetti, Soledad,Girardini, Javier E.,Sarotti, Ariel M.,Spanevello, Rolando A.,Suárez, Alejandra G.,Tsai, Yi-hsuan
supporting information

(2020/06/03)

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate
An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.
Kumar, Pravin,Kapur, Manmohan
supporting information
p. 5855 - 5860
(2020/07/30)

Uncommon overoxidative catalytic activity in a new halo-tolerant alcohol dehydrogenase
Alcohol dehydrogenases (ADH) are versatile and useful enzymes employed as biocatalysts, especially for the selective oxidation of primary and secondary alcohols, and for the reduction of carbonyl moieties. A new alcohol dehydrogenase (HeADH-II) has been identified from the genome of the halo-adapted bacterium Halomonas elongata, which proved stable in the presence of polar organic solvents and salt exposure. Unusual for this class of enzymes, HeADH-II lacks enantiopreference and is capable of oxidizing both alcohols and aldehydes, enabling a direct overoxidation of primary alcohols to carboxylic acids. HeADH-II was coupled with a NADH-oxidase from Lactobacillus pentosus (LpNOX) to increase the process yields and allowing recycling of the cofactor. The enzymatic oxidation of primary alcohols was also paired with in situ condensation of the intermediate aldehydes with hydroxylamine to prepare the corresponding aldoximes, with particular attention to perillartine (a powerful sweetener), whose enzymatic synthesis starting from natural sources, leads to an equally natural product.
Contente, Martina L.,Fiore, Noemi,Cannazza, Pietro,Roura Padrosa, David,Molinari, Francesco,Gourlay, Louise,Paradisi, Francesca
supporting information
p. 5679 - 5685
(2020/09/17)

Synthetic method of cinnamonitrile
The invention discloses a synthetic method of cinnamonitrile, and cinnamaldehyde is used as a starting raw material to undergo condensation reaction and elimination reaction to synthesize the cinnamonitrile. According to the method disclosed by the invention, filter liquor is reused in the condensation reaction, so that zero emission of wastewater of the condensation reaction is realized, the yield of cinnamaldehyde oxime is increased, unit consumption of the cinnamaldehyde and hydroxylamine hydrochloride is reduced, and a byproduct sodium chloride or potassium chloride solid is produced; a catalyst is added in the elimination reaction reaction, the esterification capability of acetic anhydride is improved, elimination reaction rate is increased, and the unit consumption of the acetic anhydride is reduced.
-
Paragraph 0047; 0048-0051; 0054-0058; 0061-0065; 0068-0072

(2019/02/04)

Visible light-induced direct conversion of aldehydes into nitriles in aqueous medium using Co@g-C3N4 as photocatalyst
Unprecedented Co@g-C3N4 catalyzed visible light driven efficient conversion of a variety of aldehydes into corresponding nitriles is reported. Operational simplicity, excellent yield of pure products (87–94%), ambient reaction condition, using aqueous methanol as solvent, visible-light photocatalysis are the salient features of envisaged methodology for direct conversion of aldehydes into nitriles. Furthermore, reusability of Co@g-C3N4 was checked up to five runs and it was noticed that there was no substantial change in morphology as well as the catalytic efficiency of catalyst.
Verma, Fooleswar,Shukla, Prashant,Bhardiya, Smita R.,Singh, Manorama,Rai, Ankita,Rai, Vijai K.
p. 76 - 81
(2018/11/10)

Palladium-Catalyzed Annulation of Aryltriazoles and Arylisoxazoles with Alkynes
We developed herein a palladium-catalyzed annulation of aryltriazoles and arylisoxazoles with internal alkynes via C?H bond activation process. 4,5-disubstituted-3H-naphtho[1,2-d][1,2,3]triazoles and 4,5-disubstituted-naphtho[2,1-d]isoxazoles could be afforded in good yields, respectively. The starting materials are readily available and the scope and applications of this transformation were explored. The reaction offers a practical approach to naphthalene fused heterocycles. (Figure presented.).
Yuan, Hairui,Wang, Min,Xu, Zhenghu,Gao, Hongyin
supporting information
p. 4386 - 4392
(2019/08/12)

Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes
Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.
Yang, Kai,Zhang, Feng,Fang, Tongchang,Zhang, Guan,Song, Qiuling
supporting information
p. 13421 - 13426
(2019/08/20)

SO 2 F 2 -Promoted Dehydration of Aldoximes: A Rapid and Simple Access to Nitriles
A rapid, simple and mild process for the dehydration of aldoximes to give the corresponding nitriles, which utilizes SO 2 F 2 as an efficient reagent, has been developed. A variety of (hetero)arene, alkene, alkyne and aliphatic aldoximes proceeded with high efficiency to afford nitriles in excellent to quantitative yields with great functional group compatibilities in acetonitrile under ambient conditions. Furthermore, an eco-friendly synthetic protocol to access nitriles from aldehydes with ortho -, meta - and para -nitrile groups was also described in aqueous methanol by using inorganic base Na 2 CO 3, and a one-pot synthetic strategy to generate nitriles from aldehydes was proved to be feasible.
Ding, Chengrong,Mei, Guangyao,Wang, Haibo,Zhang, Guofu,Zhao, Yiyong
supporting information
p. 1484 - 1488
(2019/07/15)

Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)
Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.
Keyhaniyan, Mahdi,Shiri, Ali,Eshghi, Hossein,Khojastehnezhad, Amir
(2018/05/23)

Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.
Bi, Fangchao,Song, Di,Zhang, Nan,Liu, Zhiyang,Gu, Xinjie,Hu, Chaoyu,Cai, Xiaokang,Venter, Henrietta,Ma, Shutao
p. 90 - 103
(2018/10/04)

Selective and facile synthesis of α,β-unsaturated nitriles and amides with N-hydroxyphthalimide as the nitrogen source
The direct conversion of α,β-unsaturated aldehydes to corresponding nitriles promoted by Pd(OAc)2 and phthalic acid which was hydrolyzed from N-hydroxyphthalimide (NHPI) has been disclosed. Additionally, it was found that when water was used as the solvent, α,β-unsaturated amides was obtained as the main products in good to excellent yields. It was first reported that NHPI was utilized as the nitrogen source to synthesize α,β-unsaturated nitriles and amides from aldehydes. Control experiment demonstrated that aldehydes undergo a process of oximation and dehydration to form nitriles and amides.
Yan, Yiyan,Xu, Xiaohe,Jie, Xiaokang,Cheng, Jingya,Bai, Renren,Shuai, Qi,Xie, Yuanyuan
p. 2793 - 2796
(2018/06/25)

An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
supporting information
p. 1990 - 1995
(2017/06/09)

Ultrasonic-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles via various terminal acetylenes and azide and their quorum sensing inhibition
An efficient synthesis of 1,4-disubstituted 1,2,3-triazole derivatives was studied. 1,4-Disubstituted 1,2,3-triazoles containing isoxazole and thymidine structures were synthesized in 84–96% yields starting from various terminal isoxazole ether alkynes and β-thymidine azide derivatives via a 1,3-dispolar cycloaddition using copper acetate, sodium ascorbate as the catalyst under ultrasonic assisted condition. All the target compounds were characterized by HRMS, FT-IR, 1H NMR and 13C NMR spectroscopy. Furthermore, the quorum sensing inhibitory activities of synthesized compounds were evaluated with Chromobacterium violaceum (C. Violaceum CV026) based on their inhibition of violacein production, with compound C10-HSL as a positive control. The compounds 8a, 8c and 8f exhibited considerable levels of inhibitory activity against violacein production, and IC50 values were 217?±?19, 223?±?20 and 42.8?±?4.5?μM, respectively, which highlighted the potential of these compounds as lead structures for further research towards the development of novel QS inhibitors.
Zhang, Da-wei,Zhang, Yu-min,Li, Jing,Zhao, Tian-qi,Gu, Qiang,Lin, Feng
p. 343 - 353
(2016/12/23)

Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes
An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(iii) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support the iron salt in the promotion of the transformation.
Gao, Sen,Gao, Liming,Meng, Hong,Luo, Meiming,Zeng, Xiaoming
supporting information
p. 9886 - 9889
(2017/09/11)

A hydrophilic inorganic framework based on a sandwich polyoxometalate: Unusual chemoselectivity for aldehydes/ketones with in situ generated hydroxylamine
A hydrophilic inorganic porous catalyst was prepared via the hydrothermal method. The combination of [WZn3(H2O)2(ZnW9O34)2]12- and Co(ii) provides a synergistical catalytic way to promote oximation of aldehyde/ketone with in situ generated hydroxylamine that initially produces an oxime, which further either dehydrates into a nitrile or undergoes a Beckmann rearrangement to form an amide.
Xing, Songzhu,Han, Qiuxia,Shi, Zhuolin,Wang, Shugai,Yang, Peipei,Wu, Qiang,Li, Mingxue
supporting information
p. 11537 - 11541
(2017/09/18)

Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles
We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility.
Zhang, Qi,Zhang, Linjing,Tang, Chaojun,Luo, Huan,Cai, Xuediao,Chai, Yonghai
p. 6935 - 6942
(2016/10/14)

METHOD FOR PRODUCING ALDOXIME COMPOUND
PROBLEM TO BE SOLVED: To provide a method for producing an aldoxime compound using no expensive catalysts and reagents and also requiring no severe reaction conditions. SOLUTION: There is provided a method for producing an aldoxime compound containing a process where an aldehyde compound and an oxime compound are brought into trans oximation reaction in the presence of perchloric acid and/or the metallic salt of perchloric acid in an organic solvent and water. The metallic salt of perchloric acid is preferably ferric perchlorate, cobalt perchlorate, nickel perchlorate, zinc perchlorate, aluminum perchlorate or calcium perchlorate. Also, the organic solvent is preferably methylene chloride and/or ethylene dichloride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
-
Paragraph 0027; 0039-0040

(2018/10/16)

Br?nsted acid catalyzed transoximation reaction: Synthesis of aldoximes and ketoximes without use of hydroxylamine salts
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
supporting information
p. 5788 - 5793
(2016/11/06)

ZnO Nanotube as reusable catalyst in the efficient and selective oximation reaction of carbonyl groups under solvent free conditions
A convenient and efficient procedure for the selective protection of carbonyl groups in the presence of ZnO nanotube, as reusable eco-friendly catalyst under solvent free conditions is described. The salient features of this methodology are cheaper process, easy availability of the catalyst, versatility, and the catalyst can be recovered after completion of the reaction and can be recycled without affecting the catalytic property.
Kiasat, Ali Reza,Javaherian, Mohammad,Daei, Mina,Farbod, Mansoor
p. 875 - 880
(2015/11/24)

Efficient synthesis of bis-isoxazole ethers via 1,3-dipolar cycloaddition catalysed by Zn/Zn2+ and their antifungal activities
An efficient method was developed for synthesising isoxazoles. A series of novel bis-isoxazole ether compounds VI, VII and VIII were synthesised starting from different substituted aldehydes (I) via a 1,3-dispolar cycloaddition using Zn/Zn2+ as a catalyst; these were characterised by FT-IR, HRMS, 1H NMR and 13C NMR spectroscopy. In addition, the antimicrobial properties of the synthesised products were investigated. The synthesised compounds exhibited significant antifungal activities in comparison with the standard drugs, fluconazole and itraconazole. It was found that Candida albicans was sensitive to 2-substituted phenyl bis-isoxazole ethers bearing pyridyl.
Zhang, Da-Wei,Lin, Feng,Li, Bo-Chao,Liu, Hong-Wei,Zhao, Tian-Qi,Zhang, Yu-Min,Gu, Qiang
p. 1500 - 1511
(2015/09/15)

Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles
A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.
Lei, Xiaoqiang,Li, Longbo,He, Yu-Peng,Tang, Yefeng
supporting information
p. 5224 - 5227
(2015/11/18)

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E
The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally 1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.
Keita, Massaba,Vandamme, Mathilde,Paquin, Jean-Fran?ois
p. 3758 - 3766
(2015/11/28)

Tandem and Selective Conversion of Tetrahydropyranyl and Silyl Ethers to Oximes Catalyzed with Trichloroisocyanuric Acid
Direct and oxidative conversion of tetrahydropyranyl and silyl ethers to oximes is described using trichloroisocyanuric acid (TCCA) as a relatively stable and inexpensive oxidant surprisingly in a catalytic amount and hydroxylamine hydrochloride under solvent-free conditions. Oximes can be synthesized from these protected alcohols in the presence of some other functional groups with excellent chemoselectivity using the present tandem catalytic method.
Aghapour, Ghasem,Abbaszadeh, Zeinab
p. 1464 - 1470
(2015/09/01)

Kinetic resolution of primary allylic amines via palladium-catalyzed asymmetric allylic alkylation of malononitriles
A range of primary allylic amines were resolved with selectivity factors of up to 491 through [Pd(allyl)Cl]2/(S)-BINAP-catalyzed and mesitylsulfonyl hydrazide-accelerated asymmetric allylic alkylation of malononitriles involving enantioselectiv
Wang, Yong,Xu, Ya-Nan,Fang, Guo-Sheng,Kang, Hong-Jian,Gu, Yonghong,Tian, Shi-Kai
supporting information
p. 5367 - 5371
(2015/05/20)

Dual nature of polyethylene glycol under microwave irradiation for the clean synthesis of oximes
Polyethylene glycol (PEG-400 and PEG-600) is an efficient, inexpensive, and recyclable homogeneous medium and catalyst (dual nature) for the clean synthesis of oximes (and aldoximes) under microwave irradiation in the absence of acid and base catalysts. Both aliphatic and aromatic aldehydes/ketones give satisfactory results under microwave irradiation within a short time. Graphical abstract: [Figure not available: see fulltext.]
Dutta, Papia,Dutta, Arup Kumar,Sarma, Parishmita,Borah, Ruli
p. 505 - 508
(2014/03/21)

One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers
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
p. 101 - 108
(2014/08/18)

Metal-Free: A novel and efficient aerobic oxidation of primary amines to oximes using N, N', N''-trihydroxyisocyanuric acid and acetaldoxime as catalysts in water
A general, efficient, and metal-free method for aerobic oxidation of aromatic primary amines to the corresponding oximes catalyzed by N,N',N''-trihydroxyisocyanuric acid and acetaldoxime with water as solvent is described. This practical method can use air as economic and green oxidant, water as green solvent, and tolerates a wide range of substrates, which can afford the target oximes in moderate to good yields. Georg Thieme Verlag Stuttgart. New York.
Yu, Jiatao,Lu, Ming
p. 1873 - 1878
(2014/08/18)

A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl3 for aerobic oxidation of primary amines to oximes
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
supporting information
p. 5751 - 5755
(2015/02/02)

Synthesis and anti-inflammatory activity of aromatic glucosinolates
Aromatic GLs are important members of the glucosinolate family of compounds because of their potential biological activity and medicinal properties. This study has shown success in the high yielding synthesis of some important aromatic GLs as well as the results of testing for anti-inflammatory properties of the synthetic GLs. 3,4-Dimethoxyphenylglucosinolate was found to be the most active anti-inflammatory of the seven glucosinolates assayed.
Vo, Quan V.,Trenerry, Craige,Rochfort, Simone,Wadeson, Jenny,Leyton, Carolina,Hughes, Andrew B.
p. 5945 - 5954
(2013/09/23)

Oximation of carbonyl compounds by basic alumina supported amberlite IRA 400 under microwave energy and pestle/mortar
An efficient and novel method for the preparation of oximes from carbonyl compounds under solventless conditions.
Singh, Sanjeev Pratap,Singh
experimental part
p. 1354 - 1356
(2012/09/21)

Acetohydroxamic acid: A new reagent for efficient synthesis of nitriles directly from aldehydes using Bi(OTf)3 as the catalyst
An efficient method for the preparation of nitriles directly from aldehydes by reaction with AHA using Bi(OTf)3 as the catalyst is described. Bi(OTf)3 is shown to be an efficient catalyst also for the conversion of aldoximes into nitriles.
Sridhar, Madabhushi,Reddy, Mallu Kishore Kumar,Sairam, Vangipuram Venkata,Raveendra, Jillella,Godala, Kondal Reddy,Narsaiah, Chinthala,Ramanaiah, Beeram China,Reddy, Cirandur Suresh
scheme or table
p. 3421 - 3424
(2012/08/08)

Efficient synthesis of oxime using o-tbs-n-tosylhydroxylamine: Preparation of (2z)-4-(benzyloxy)but-2-enal oxime
-
Kitahara, Katsushi,Toma, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
p. 480 - 490
(2014/04/17)

Method for the selective formation of dimethyl acetals in the presence of hydroxylamine
An inexpensive and mild method for the formation of dimethyl acetals from the corresponding aldehydes is achieved using hydroxylamine and methanol under neutral conditions at room temperature. Notably, the reaction is selective for aldehydes in the presence of ketones, rendering this an example of a chemoselective acetalization. For saturated, sterically accessible aldehydes, catalytic amounts of hydroxylamine may be employed to attain the corresponding dimethyl acetal as the sole product in good to excellent yield. Unsaturated and hindered aldehydes required stoichiometric amounts of hydroxylamine but provided dimethyl acetals as the major product in typically excellent yield. In some cases, the corresponding oxime was also observed but may be separated from the acetal by flash column chromatography or distillation. The involvement of an intermediate oxime compound is postulated. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
Mickelsen, Ky J.,Tajc, Chelsea M.,Greenwood, Kevin R.,Browder, Cindy C.
experimental part
p. 186 - 194
(2011/10/31)

Selective tandem synthesis of oximes from benzylic alcohols catalyzed with 2, 3-dichloro-5, 6-dicyanobenzoquinone
In spite of many reports in the literature concerning with oxidation of benzylic alcohols to carbonyl compounds with 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) in stoichiometric amounts or even more, we surprisingly found that benzylic alcohols are directly oxidized to oximes using a catalytic amount of DDQ in the presence of hydroxylamine hydrochloride under solvent-free conditions. The present tandem catalytic method can be efficiently used for preparation of oximes in the presence of some other functional groups with excellent chemoselectivity.
Aghapour, Ghasem,Mohamadian, Samaneh
experimental part
p. 1209 - 1212
(2012/07/13)

Efficient microwave-assisted synthesis of oximes from acetohydroxamic acid and carbonyl compounds using BF3·OEt2 as the catalyst
An efficient synthesis of oximes by reaction of carbonyls with acetohydroxamic acid using BF3·OEt2 as a catalyst is described.
Sridhar, Madabhushi,Narsaiah, Chinthala,Raveendra, Jillella,Kondal Reddy, Godala,Kishore Kumar Reddy, Mallu,China Ramanaiah, Beeram
experimental part
p. 4701 - 4704
(2011/09/20)

Microwave-promoted one-pot conversion of alcohols to oximes using 1-methylimidazolium nitrate, [Hmim][NO3], as a green promoter and medium
A wide variety of oximes were prepared from different types of alcohols with hydroxylamine hydrochloride using 1-methylimidaziloum nitrate, [Hmim][NO3], ionic liquid as a reaction medium and promoter under microwave irradiation. This protocol provides a one-pot oxime synthesis with high yields that is facile, eco-friendly and the ionic liquid can be recovered and reused.
Mirjafari, Arsalan,Mobarrez, Niloufar,O'Brien, Richard A.,Davis Jr, James H.,Noei, Jalil
experimental part
p. 1065 - 1070
(2012/03/11)

An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.
Augustine, John Kallikat,Kumar, Rajesha,Bombrun, Agnes,Mandal, Ashis Baran
experimental part
p. 1074 - 1077
(2011/03/22)

Au/Ag-cocatalyzed aldoximes to amides rearrangement under solvent- and acid-free conditions
(Chemical Equation Presented) The gold/silver-cocatalyzed conversion of aldoximes into primary amides is reported. The reaction, which proceeds under neat and acid-free conditions, allows for the conversion of a range of aldoximes, and is a rare example of cooperative catalysis involving well-defined gold species.
Ramon, Ruben S.,Bosson, Johann,Diez-Gonzalez, Silvia,Marion, Nicolas,Nolan, Steven P.
supporting information; experimental part
p. 1197 - 1202
(2010/04/02)

A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids
We have developed a chemoselective, simple and efficient method for the preparation of aldoximes using microwave irradiation in the presence of tribenzylamine or 1,4-diazabicyclo[2.2.2]octane or 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide as bases and useful precursors for in situ generation of ionic liquids.
Hajipour,Rafiee,Ruoho
experimental part
p. 114 - 118
(2010/10/21)

Simple, efficient and green synthesis of oximes under ultrasound irradiation
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
p. 192 - 194
(2013/01/09)

An efficient transformation from benzyl or allyl halides to aryl and alkenyl nitriles
(Figure presented) A novel approach to aryl or alkenyl nitriles from benzyl and allyl halides has been developed. A tandem TBAB-catalyzed substitution and the subsequent novel oxidative rearrangement are involved in this transformation. To the best of our knowledge, this is the first transformation from allyl halides to alkenyl nitriles. The broad reaction scope and the mild conditions may make these methods of use in organic synthesis.
Zhou, Wang,Xu, Jiaojiao,Zhang, Liangren,Jiao, Ning
supporting information; scheme or table
p. 2888 - 2891
(2010/08/22)

Gold supported on hydroxyapatite as a versatile multifunctional catalyst for the direct tandem synthesis of imines and oximes
-
Sun, Hao,Su, Fang-Zheng,Ni, Ji,Cao, Yong,He, He-Yong,Fan, Kang-Nian
supporting information; experimental part
p. 4390 - 4393
(2009/10/20)

O-TBS-N-tosylhydroxylamine: A reagent for facile conversion of alcohols to oximes
(Chemical Equation Presented) A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.
Kitahara, Katsushi,Toma, Tatsuya,Shimokawa, Jun,Fukuyama, Tohru
supporting information; experimental part
p. 2259 - 2261
(2009/05/26)

Potent inhibitors of lipoprotein-associated phospholipase A2: Benzaldehyde O-heterocycle-4-carbonyloxime
A series of multi-substituted oximes were prepared and their potencies for inhibiting lipoprotein-associated phospholipase A2 (Lp-PLA2) activity were evaluated in vitro. Among them, compounds 3a, 3b, and 3m were identified to display a micromolar potency for inhibiting Lp-PLA2 in whole human plasma and isolated human LDL. Based on these results, structure-activity relationship was studied on modification of three parts of R1, R2, and R3 to identify a potent pharmacophore for Lp-PLA2. In an attempt to introduce various functional groups at R2 and R3, we discovered that replacement of less lipophilic groups led to an increase of inhibitory activity. Among the tested oxime derivatives, cyano- and morpholino-substituted analogue 4f at R2 and R3 had the highest potency with an IC50 value of 0.05 μM in whole human plasma.
Jeong, Hyung Jae,Park, Yong-Dae,Park, Ho-Yong,Jeong, Il Yun,Jeong, Tae-Sook,Lee, Woo Song
p. 5576 - 5579
(2007/10/03)

Metalloporphyrin and heteropoly acid catalyzed oxidation of C=NOH bonds in an ionic liquid: Biomimetic models of nitric oxide synthase
Water soluble iron(III) porphyrins and phosphotungstic acid in an ionic liquid are effective catalysts for the H2O2 mediated oxidation of the CNOH bond in N-hydroxyarginine and other oximes. The carbonyl compounds generated as the oxidation products can be easily isolated from the reaction media. These systems serve as biomimetic models of nitric oxide synthase (NOS) and the catalyst immobilized in an ionic liquid can be easily recycled and reused.
Jain, Nidhi,Kumar, Anil,Chauhan, Shive M.S.
p. 2599 - 2602
(2007/10/03)