- Solid-phase synthesis of oximes
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In an extremely fast, high efficient and novel method, the reaction of hydroxylamine hydrochloride with a number of aldehydes and ketones under solventless 'dry' condition gave oximes in quantitative yield.
- Hajipour,Mohammadpoor-Baltork,Nikbaghat,Imanzadeh
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Read Online
- Quinone-sensitized steady-state photolysis of acetophenone oximes under aerobic conditions: Kinetics and product studies
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Oxidation of oximes via photosensitized electron transfer (PET) results in the formation of the corresponding ketones as the major product via oxime radical cations and iminoxyl radicals. The influence of electron-releasing and electron-accepting substituents on these reactions was studied. The observed substituent effect strongly supports formation of iminoxyl radicals from the oximes via an electron transfer-proton transfer sequence rather than direct hydrogen atom abstraction. Correlation of the relative conversion of the oximes with Hammett parameters shows that radical effects dominate for the meta-substituted acetophenone oximes (ρrad/ ρpol = 5.4; r2 = 0.93), whereas the para-substituted oximes are influenced almost equally by radical and ionic effects (ρrad/ ρpol = -1.1; r2 = 0.98). From these data sets we conclude that the follow-up reactions proceed through a number of intermediates with both radical and ionic character. This was confirmed by product studies with the use of an isotopically labeled nucleophile. In addition to the major oxidation product (ketone), a chlorine-containing product was often identified as well. Studies on the formation of this product show that the most likely pathway is either via a direct nucleophilic addition in a complex formed between the oxime radical cation and the chloranil radical anion or via a radical substitution (SH2) mechanism. These studies show that with the increasing use of oximes as drugs and pesticides, intake of these chemicals followed by enzymatic oxidation may result in the formation of a variety of reactive intermediates, which may lead to cell and tissue damage.
- Park, Adriana,Kosareff, Nicole M.,Kim, Jason S.,De Lijser, H. J. Peter
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Read Online
- In situ functionalized sulfonic copolymer toward recyclable heterogeneous catalyst for efficient Beckmann rearrangement of cyclohexanone oxime
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Exploring environmentally friendly, efficient and recyclable heterogeneous catalysts for low-temperature liquid-phase organic reactions are important for the development of green and sustainable processes. In this work, we applied an in situ sulfonated polymeric solid acid H-PDVB-SO3H for catalyzing liquid-phase Beckmann rearrangements for the first time, with post-sulfonated sample and other various counterparts as control catalysts. H-PDVB-SO3H was prepared by copolymerization of divinylbenzene with sodium p-styrene sulfonate under solvothermal condition, followed by ion-exchanging to convert the polymer into proton form. It possessed a large surface area, plenty of mesopores and high sulfur content, and exhibited the high yield to ε-caprolactam (75%) with quite steady reusability in the heterogeneous Beckmann rearrangement of cyclohexanone oxime. The catalyst also showed good substrate compatibility with such a high reaction rate that the reaction time was as short as 1 h. No any co-catalysts or metals were used in the catalytic system, making the catalyst an environmentally friendly and efficient candidate for Beckmann rearrangements.
- Li, Difan,Mao, Dan,Li, Jing,Zhou, Yu,Wang, Jun
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Read Online
- Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes
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The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.
- Li, Xiaolan,Sun, Kai,Shen, Wenjuan,Zhang, Yong,Lu, Ming-Zhu,Luo, Xuzhong,Luo, Haiqing
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supporting information
p. 31 - 36
(2021/01/09)
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- Trifluoroacetic Acid Hydroxylamine System as Organocatalyst Reagent in a One-Pot Salt Free Process for the Synthesis of Caprolactam and Amides of Industrial Interest
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In this work we studied the reactivity of the Trifluoroacetic acid hydroxylamine system in the one step salt free synthesis of amides from ketones. A particular regards was paid to the caprolactam synthesis because of its industrial relevance. Synthesis, reactivity and characterization of the hydroxylamine trifluoroacetate is given. Fast oximation reaction of several ketones was gained at room temperature (1?h of reaction quantitative conversion for several ketones). In the same reactor, by raising the temperature at 383?K, the Beckmann rearrangement of the so obtained oximes is easily accomplished in the presence of three equivalent of TFA. The possibility of obtaining the trifluoroacetate of the hydroxylamine with a modified nitric acid hydrogenation reactions was verified, too. Reuse of solvent and trifluoroacetic acid is easily achieved by distillation. Graphical abstract: Salt free one-pot caprolactam and amides process catalyzed by CF3COOH, in the presence of NH2OH TFA as the oximation agent.[Figure not available: see fulltext.].
- Manente,Pietrobon,Ronchin,Vavasori
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p. 3543 - 3549
(2021/03/30)
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- Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations
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A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.
- Upare, Atul,Chouhan, Neeraj Kumar,Ramaraju, Andhavaram,Sridhar, Balasubramanian,Bathula, Surendar Reddy
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supporting information
p. 1743 - 1746
(2020/03/17)
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- Copper-Catalyzed Annulation of Oxime Acetates with α-Amino Acid Ester Derivatives: Synthesis of 3-Sulfonamido/Imino 4-Pyrrolin-2-ones
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A copper-catalyzed annulation of oxime acetates and α-amino acid ester derivatives for the easy preparation of 4-pyrrolin-2-ones bearing a 3-amino group has been developed. This process features the oxidation of amines with oxime esters as the internal oxidant to produce the active 1,3-dinucleophilic and 1,2-dielectrophilic species concurrently. The subsequent nucleophilic cyclization realizes the efficient construction of 4-pyrrolin-2-one derivatives.
- Miao, Chun-Bao,Zheng, An-Qi,Zhou, Li-Jin,Lyu, Xinyu,Yang, Hai-Tao
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supporting information
p. 3381 - 3385
(2020/04/21)
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- CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles
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An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.
- Gudimella, Santosh K.,Kaur, Amanpreet,Kumar, Ram,Samanta, Sampak
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supporting information
(2020/07/08)
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- Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls
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A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.
- Meng, Huanxin,Xu, Zhenhua,Qu, Zhonghua,Huang, Huawen,Deng, Guo-Jun
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supporting information
p. 6117 - 6121
(2020/08/12)
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- Preparation method of pyrimidine salicylate oxime ester compound and application of compound as herbicide
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The invention discloses a preparation method of a pyrimidine salicylate oxime ester compound and application of the compound as a herbicide, belongs to the technical field of herbicides, and relates to the application of the herbicide in selectively controlling gramineous weeds and broadleaf weeds for crops. The compound is a pyrithiobac oxime ester compound. The preparation method includes the following steps that acids of pyrithiobac are condensed with substituted acetophenoxime in the presence of an organic solvent and a condensation agent to prepare a (I) compound. At 45 g a.i./hm, thecompound can effectively control echinochloa crusgalli, eleusineindica, setaria viridis, amaranthus retroflexus, portulaca oleracea, chenopodium album and other grassy weeds and broadleaf weeds, can serve as a candidate herbicide in a cotton field and has potential industrial application. Meanwhile, the compound is environmentally friendly, low in toxicity and highly safe for crops such as cotton.The invention provides a preparation technology of the efficient and safe novel pyrimidine salicylate oxime ester compound with the herbicidal activity, the compound can be massively produced, the yield is high and the purity is high.
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Paragraph 0105; 0106
(2019/10/22)
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- SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
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A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
- Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
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supporting information
p. 4911 - 4915
(2019/07/31)
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- Copper-Catalyzed Three-Component Domino Cyclization for the Synthesis of 4-Aryl-5-(arythio)-2-(trifluoromethyl)oxazoles
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A copper-catalyzed oxidative cyclization of oxime, arylthiol, and trifluoroacetic anhydride for the construction of trisubstituted oxazoles has been developed. This transformation combines N-O bond cleavage, C-H functionalization, and intramolecular annulation, providing a practical protocol for the introduction of a trifluoromethyl (-CF3) group at oxazole rings.
- Xiao, Fuhong,Yuan, Shanshan,Huang, Huawen,Zhang, Feng,Deng, Guo-Jun
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supporting information
p. 8533 - 8536
(2019/10/17)
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- Beckmann rearrangement of ketoxime catalyzed by N-methyl-imidazolium hydrosulfate
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Beckmann rearrangement of ketoxime catalyzed by acidic ionic liquid-N-methyl-imidazolium hydrosulfate was studied. Rearrangement of benzophenone oxime gave the desirable product with 45% yield at 90 ?C. When co-catalyst P2O5 was added, the yield could be improved to 91%. The catalyst could be reused three cycles with the same efficiency. Finally, reactions of other ketoximes were also investigated.
- Hu, Hongyu,Cai, Xuting,Xu, Zhuying,Yan, Xiaoyang,Zhao, Shengxian
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- Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
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A novel copper-catalyzed annulation of oxime acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(iii) intermediates were involved. In addition, this protocol proceeded under redox-neutral conditions and did not require additives or ligands.
- Zhu, Zhongzhi,Tang, Xiaodong,Cen, Jinghe,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 3767 - 3770
(2018/04/17)
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- Cu-Catalyzed Coupling of O-Acyl Oximes with Isatins: Domino Rearrangement Strategy for Direct Access to Quinoline-4-Carboxamides by C–N Bond Cleavage
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A mild domino rearrangement strategy for the direct access to substituted quinoline-4-carboxamides has been developed. This copper-catalyzed coupling reaction of O-acyl oximes with isatins in the presence of molecular oxygen as the sole oxidizing agent proceeds through a ring expansion of the isatins through cleavage of the two C–N bonds.
- Ramaraju, Andhavaram,Chouhan, Neeraj Kumar,Ravi, Owk,Sridhar, Balasubramanian,Bathula, Surendar Reddy
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p. 2963 - 2971
(2018/06/27)
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- Elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles using trifluoroacetic anhydride as reagent
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An elemental tellurium mediated synthesis of 2-(trifluoromethyl)oxazoles from the reaction of acetophenone oxime acetates with trifluoroacetic anhydride has been developed. This new tandem cyclization proceeds in good to excellent yields via a SET reduction followed by a 5-endo-trig pathway. Some of the title compounds showed fungicidal and insecticidal activities.
- Luo, Beibei,Weng, Zhiqiang
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supporting information
p. 10750 - 10753
(2018/09/29)
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- Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes
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Transition-metal or iodine catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.
- Upare, Atul,Sathyanarayana, Pochampalli,Kore, Ranjith,Sharma, Komal,Bathula, Surendar Reddy
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supporting information
p. 2430 - 2433
(2018/05/23)
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- Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions
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A novel and versatile method for the synthesis of 2H-imidazoles via iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides has been developed. This denitrogenative process involved N-O/N-N bond cleavages and two C-N bond formations to furnish 2,4-substituted 2H-imidazoles. This protocol was performed under mild reaction conditions and needed no additives or ligands. Furthermore, this is a green reaction involving oxime acetate as internal oxidant, acetic acid, and nitrogen as byproducts.
- Zhu, Zhongzhi,Tang, Xiaodong,Li, Jianxiao,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
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supporting information
p. 1370 - 1373
(2017/03/23)
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- The fullerene dieno 3, 4 - dihydro pyrrole derivative and its preparation method
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The invention relates to a fullereno-3,4-dihydropyrrole derivative and a preparation method thereof. The compound has the structure as shown in the specification, wherein R1 is -Ar or -CH3; R2 is -H or -CH3; and R3 is -H, -CH3 or -Ph. The novel [60] fullereno-3,4-dihydropyrrole compound indicates that [60]fullerene exhibits uniqueness in structure and has specialty in reactivity which is deficient in general substances. As an important intermediate of fine chemical products, the product dihydropyrrole has wide application in the fields such as medicines, pesticides, coatings, daily chemicals and polymer materials.
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Paragraph 0036
(2017/10/31)
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- Palladium-Catalyzed C-H Functionalization of Aromatic Oximes: A Strategy for the Synthesis of Isoquinolines
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An efficient strategy for synthesis of isoquinolines via Pd(II)-catalyzed cyclization reaction of oximes with vinyl azides or homocoupling of oximes is reported. Oximes could serve as a directing group and an internal oxidant in the transformation. This reaction features good functional group tolerance and provides a useful protocol for the synthesis of different kinds of isoquinolines under mild conditions. Some control experiments and 15N isotope labeling experiments were conducted for the mechanistic research. (Chemical Equation Presented).
- Zhu, Zhongzhi,Tang, Xiaodong,Li, Xianwei,Wu, Wanqing,Deng, Guohua,Jiang, Huanfeng
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p. 1401 - 1409
(2016/03/01)
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- ZnO Nanotube as reusable catalyst in the efficient and selective oximation reaction of carbonyl groups under solvent free conditions
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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
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p. 875 - 880
(2015/11/24)
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- AIEE active perylene bisimide supported mercury nanoparticles for synthesis of amides via aldoximes/ketoximes rearrangement
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Aggregates of perylene bisimide (PBI) derivative 3 serve as reactors and stabilizers for the preparation of mercury nanoparticles (HgNPs) which exhibit excellent catalytic efficiency in the conversion of aldoximes/ketoximes into primary/secondary amides via Beckmann rearrangement. This journal is
- Kaur, Sandeep,Kumar, Manoj,Bhalla, Vandana
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supporting information
p. 4085 - 4088
(2015/03/18)
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- Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
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Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.
- Das, Braja Gopal,Nallagonda, Rajender,Dey, Dhananjay,Ghorai, Prasanta
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supporting information
p. 12601 - 12605
(2015/09/01)
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- Cobalt(III)-Catalyzed Dehydrative [4+2] Annulation of Oxime with Alkyne by C-H and N-OH Activation
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Efficient, scalable cobalt-catalyzed redox-neutral [4+2] annulation of readily available oximes and alkyne is reported. The developed synthetic methodology is widely applicable and tolerates various functional groups including heterocycles. A stable CpCoIII neutral complex is employed as the catalyst for this redox-neutral [4+2] annulation reaction, which progresses smoothly by way of a reversible cyclometallation without any external oxidizing agent, and produces only water as the side product.
- Sen, Malay,Kalsi, Deepti,Sundararaju, Basker
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supporting information
p. 15529 - 15533
(2015/11/03)
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- Direct catalytic enantio- and diastereoselective Mannich reaction of isocyanoacetates and ketimines
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A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom by a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. When a combination of a cinchona-derived aminophosphine precatalyst and silver oxide was employed as a binary catalyst system, good reactivity, high diastereoselectivities (up to 99:1 d.r.), and excellent enantioselectivities (up to 99 % ee) were obtained for a range of substrates. Binary catalyst system: A catalytic asymmetric synthesis of imidazolines with a fully substituted β-carbon atom through a Mannich-type addition/cyclization reaction of isocyanoacetate pronucleophiles and N-diphenylphosphinoyl ketimines has been developed. By employing a cinchona-derived aminophosphine precatalyst and silver oxide as a binary catalyst system, good reactivity and high diastereo- and enantioselectivities were obtained.
- Ortin, Irene,Dixon, Darren J.
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supporting information
p. 3462 - 3465
(2014/04/03)
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- The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against the pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli
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Pyruvate dehydrogenase multienzyme complex E1 (PDHc E1) is a potential target enzyme when looking for inhibitors to combat microbial disease. In this study, we designed and synthesized a series of novel thiamin diphosphate (ThDP) analogs with triazole rin
- Feng, Lingling,He, Junbo,He, Haifeng,Zhao, Lulu,Deng, Lingfu,Zhang, Li,Zhang, Lin,Ren, Yanliang,Wan, Jian,He, Hongwu
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p. 8911 - 8918
(2014/12/11)
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- Base and solvent mediated decomposition of tosylhydrazones: Highly selective synthesis of N-alkyl substituted hydrazones, dialkylidenehydrazines, and oximes
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Base and solvent mediated decomposition of tosylhydrazones was studied. It was found that reaction of tosylhydrazones in CH3NO2 in the presence of 1 equiv of K2CO3 in 90 °C gave N-alkylated products in 52-96% yield. However, when the same reaction was carried out in mixed solvent of CH3NO2 and dioxane in the presence of 3 equiv of NaOH at 110 °C, dialkylidenehydrazines were obtained in moderate to high yield. If the reaction was carried out in mixed solvent of CH3NO2 and DMSO in the presence of 10 equiv of NaOH at 110 °C, CH3NO2 can act as the precursor of hydroxylamine and corresponding oximes were formed in up to 92% yield.
- Sha, Qiang,Wei, Yunyang
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supporting information
p. 3829 - 3835
(2013/07/05)
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- Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: Application to the ketimine nitro-Mannich reaction
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The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.
- Nunez, Marta G.,Farley, Alistair J. M.,Dixon, Darren J.
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supporting information
p. 16348 - 16351
(2013/12/04)
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- Synthesis of dibromo ketones by the reaction of the environmentally benign H2O2-HBr system with oximes
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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.
- Terentev, Alexander O.,Krylov, Igor B.,Vil, Vera A.,Pastukhova, Zhanna Yu.,Fastov, Sergey A.,Nikishin, Gennady I.
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experimental part
p. 360 - 367
(2012/08/08)
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- Microwave-assisted efficient one-step synthesis of amides from ketones and benzoxazoles from (2-hydroxyaryl) ketones with acetohydroxamic acid using sulfuric acid as the catalyst
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Efficient one-step method for the synthesis of amides directly from ketones and benzoxazoles from (2-hydroxyaryl) ketones by the reaction of acetohydroxamic acid using sulfuric acid as catalyst was described.
- Madabhushi, Sridhar,Chinthala, Narsaiah,Vangipuram, Venkata Sairam,Godala, Kondal Reddy,Jillella, Raveendra,Mallu, Kishore Kumar Reddy,Beeram, China Ramanaiah
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experimental part
p. 6103 - 6107
(2011/11/30)
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- Sodium nitrite catalyzed aerobic oxidative deoximation under mild conditions
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A mild, simple process for the effective deoximation of a wide range of ketoximes and aldoximes has been developed, which utilizes available NaNO 2 as the catalyst and molecular oxygen as the green oxidant. Notably Amberlyst-15, which acts as the initiator of NaNO2, can be reused without regeneration. This environmentally benign protocol could provide a valuable synthetic method for practical applications.
- Zhang, Guofu,Wen, Xin,Wang, Yong,Mo, Weimin,Ding, Chengrong
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supporting information; experimental part
p. 4665 - 4668
(2011/07/29)
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- Auxiliary-controlled asymmetric [3+2]-dipolar cycloaddition of azomethine ylides generated from Au-catalyzed intramolecular redox reaction of nitronyl alkynes
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As strong as an aux: An electronically-tuned hydroxylamine functions as an excellent chiral auxiliary for [3+2] cycloaddition of the azomethine ylides generated in-situ from gold-catalyzed redox reaction of alkynyl nitrones.
- Jeong, Jaewon,Yeom, Hyun-Suk,Kwon, Ohyun,Shin, Seunghoon
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supporting information; experimental part
p. 1977 - 1981
(2011/12/01)
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- An efficient one-pot synthesis of oxime ethers from alcohols using triphenylphosphine/carbon tetrachloride
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A convenient and efficient one-pot O-alkylation of oximes from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in good yields. This methodology is highly efficient O-alkylation of oximes with various structurally diverse alcohols. Semiempirical quantum-mechanic calculations (AM1) for unsymmetrical oxime ethers, indicated a lower heat of formation for Z-isomers. Georg Thieme Verlag Stuttgart - New York.
- Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Karimitabar, Fatemeh,Behrouz, Somayeh
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experimental part
p. 1724 - 1730
(2010/07/08)
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- A facile and practical synthesis of N-acetyl enamides
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(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.
- Tang, Wenjun,Capacci, Andrew,Sarvestani, Max,Wei, Xudong,Yee, Nathan K.,Senanayake, Chris H.
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supporting information; body text
p. 9528 - 9530
(2010/03/24)
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- Palladium-catalyzed annulation of acyloximes with arynes (or alkynes): Synthesis of phenanthridines and isoquinolines
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(Chemical Equation Presented) Intermolecular insertion: A palladium-catalyzed domino aminopalladation/C-H functionalization sequence has been developed, and provides access to functionalized phenanthridines and isoquinolines (see scheme; Tf = triflate, TM
- Gerfaud, Thibaud,Neuville, Luc,Zhu, Jieping
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supporting information; experimental part
p. 572 - 577
(2009/04/14)
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- Facile and efficient enantioselective strecker reaction of ketimines by chiral sodium phosphate
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A facile and efficient enantioselective Strecker reaction of ketimines catalyzed by a chiral alkali-metal salt has been developed. When 10 mol% BNPNa (BNP=1,1'-binaphthyl-2,2'-diylphosphate) prepared in situ and 10 mol% para-tert-butylortho-adamantylphenol (PBAP) were introduced into the reaction, up to 96% yield and up to 95% ee (ee=enantiomeric excess) were obtained. Both aliphatic and aromatic ketimines, especially sterically bulky cyclic ketimines derived from β-acetonaphthone, α-indanone, and α-tetralone were found suitable for this reaction. On the basis of the experimental results and previous reports, trimethylsilyl cyanide (TMSCN) was indicated to be the real reactive nucleophile despite the existence of PBAP, and a possible working model was proposed to explain the origin of the asymmetric induction. The facile availability of 1,1'-binaphthyl-2,2'-diylphosphoric acid (BNPH) and the simplicity of the procedure are beneficial for practical applications.
- Shen, Ke,Liu, Xiaohua,Cai, Yunfei,Lin, Lili,Feng, Xiaoming
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supporting information; experimental part
p. 6008 - 6014
(2010/02/28)
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- N-tert-Butyl-N-chlorocyanamide: A new reagent for the efficient preparation of gem-chloronitroso compounds
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A new reagent for the efficient preparation of gem-chloronitroso compounds has been developed. The reaction of ketoximes with N-tert-butyl-N- chlorocyanamide takes place instantaneously in carbon tetrachloride at room temperature with excellent yields under mild conditions.
- Kumar, Vinod,Kaushik
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p. 8121 - 8123
(2007/10/03)
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- Application of aryloximes as solid-phase ketone linkers.
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In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-bound oximes followed by subsequent cyclorelease to give ketone product in good yields and purities. [reaction--see text]
- Lepore, Salvatore D,Wiley, Michael R
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- Microwave enhanced synthesis of oximes from ketones
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Microwave enhanced synthesis of oximes from ketones in high yields is reported.
- Mitra, Alok Kumar,De, Aparna,Karchaudhuri, Nilay
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p. 218 - 219
(2007/10/03)
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