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Journal articles on the topic 'Oxime synthesis'

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Published: 5 June 2025
Last updated: 1 August 2025

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1

Diedrichs, Nicole, Ralf Krelaus, Ina Gedrath, and Bernhard Westermann. "Kinetic resolution of oxime esters with lipases — synthesis of enantiomerically enriched building blocks with quaternary carbon centers and formal total synthesis of perhydro histrionicotoxin." Canadian Journal of Chemistry 80, no. 6 (2002): 686–91. http://dx.doi.org/10.1139/v02-097.

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Enantiomerically enriched oximes bearing stereogenic quaternary carbon centers can be obtained by lipase-catalyzed kinetic resolution of oxime esters. Substrate specificity, solvent effects, and the use of different lipases are discussed. Kinetic resolution of butyrylated oximes by lipase PS in the presence of n-butanol gave the best ee-values of both the saponified oxime and the residual oxime ester. Subsequent stereospecific Beckmann rearrangement of an enantiomerically enriched oxime provided lactams, which could be employed for the synthesis of optically active perhydro histrionicotoxin.Ke
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2

Ali Bawa, Ramadan, and Hana Mansoure Elmajdoub. "Synthesis of Some Bridged Unsymmetrical Terphthaloyl Oxime Esters." Academic Journal of Chemistry, no. 56 (June 10, 2020): 55–57. http://dx.doi.org/10.32861/ajc.56.55.57.

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Three unsymmetrical bridged terphthaloyl acetophenone oxime esters have been synthesized throughout an esterification process between three acetophenone oximes and the terphthaloyl chloride under mild basic conditions. Spectroscopic techniques, such as IR, HNMR and mass spectrometer, were used to confirm the structures of the desired oxime esters. The yields of the resulting oxime esters ranged from 50% to 73%.
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3

Canário, Catarina, Mariana Matias, Vanessa Brito, et al. "New Estrone Oxime Derivatives: Synthesis, Cytotoxic Evaluation and Docking Studies." Molecules 26, no. 9 (2021): 2687. http://dx.doi.org/10.3390/molecules26092687.

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The interest in the introduction of the oxime group in molecules aiming to improve their biological effects is increasing. This work aimed to develop new steroidal oximes of the estrane series with potential antitumor interest. For this, several oximes were synthesized by reaction of hydroxylamine with the 17-ketone of estrone derivatives. Then, their cytotoxicity was evaluated in six cell lines. An estrogenicity assay, a cell cycle distribution analysis and a fluorescence microscopy study with Hoechst 3358 staining were performed with the most promising compound. In addition, molecular dockin
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4

Ali Bawa, Ramadan, and Hana Mansoure Elmajdoub. "Synthesis of a Number of Unsymmetrical Bridged Terphthaloyl Acetophenone Oxime Esters." Academic Journal of Chemistry, no. 57 (August 8, 2020): 98–100. http://dx.doi.org/10.32861/ajc.57.98.100.

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A number of unsymmetrical bridged terphthaloyl acetophenone oxime esters has been synthesized throughout an esterification reaction between four different acetophenone oximes and the terphthaloyl chloride in a molar ratio of (2:1) under mild basic conditions. Spectroscopic techniques, such as IR, HNMR and mass spectrometer, were used to confirm the structures of the targeted oxime esters. The yields of the obtained oxime esters ranged from 80% to 95%.
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5

Arthur-Santiago, Margarita A., Rosa María Oliart-Ros, María G. Sánchez-Otero, and Gerardo Valerio-Alfaro. "Mechanochemo-enzymatic Synthesis of Aromatic Aldehyde Oxime Esters." Natural Product Communications 13, no. 7 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300723.

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The synthesis of aromatic aldehyde oxime esters (considered fragrances, antifungal and antimicrobial compounds) was achieved by two reactions which combine the advantage of green chemistry and biocatalysis. In the first step, the mechanochemical oxime synthesis by means of grindstone milling of six solid aromatic aldehydes and hydroxylamine hydrochloride in the presence of FlorisilR, as the best support, yielded the aromatic aldehyde oximes 1–6 with high purity and good yields. In the second step the lipase catalyzed acetylation reaction at 40°C for three days of those oximes with vinyl and is
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6

Dhuguru, Jyothi, Eugene Zviagin, and Rachid Skouta. "FDA-Approved Oximes and Their Significance in Medicinal Chemistry." Pharmaceuticals 15, no. 1 (2022): 66. http://dx.doi.org/10.3390/ph15010066.

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Despite the scientific advancements, organophosphate (OP) poisoning continues to be a major threat to humans, accounting for nearly one million poisoning cases every year leading to at least 20,000 deaths worldwide. Oximes represent the most important class in medicinal chemistry, renowned for their widespread applications as OP antidotes, drugs and intermediates for the synthesis of several pharmacological derivatives. Common oxime based reactivators or nerve antidotes include pralidoxime, obidoxime, HI-6, trimedoxime and methoxime, among which pralidoxime is the only FDA-approved drug. Cepha
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7

Çil, Erol, Mustafa Arslan, and Ahmet Orhan Görgülü. "Synthesis and characterization of alkyl- and acyl-substituted oxime–phosphazenes." Canadian Journal of Chemistry 83, no. 12 (2005): 2039–45. http://dx.doi.org/10.1139/v05-223.

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Two oxime–cyclophosphazenes were prepared from the hexakis(4-formylphenoxy)cyclotriphosphazene (2) and hexakis(4-acetylphenoxy)cyclotriphosphazene (8). The reactions of these oximes with ethyl bromide, allyl bromide, propanoyl chloride, and acriloyl chloride were studied. Hexasubstituted compounds were obtained from the reactions of hexakis{4-[(hydroxyimino)methyl]phenoxy}cyclotriphosphazene (3) with ethyl bromide (4), allyl bromide (5), and propanoyl chloride (6), however, the oxime groups on 3 rearranged to nitrile (7) in the reaction of 3 with acriloyl chloride. Hexasubstituted compounds we
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8

Gulla, Mahendra, Lars Bierer, Stefan Schmidt, Leo Redcliffe, and Volker Jäger. "Bromocyclization of Unsaturated Oximes. Synthesis of Five-Membered Cyclic Nitrones (Pyrroline N-Oxides)." Zeitschrift für Naturforschung B 61, no. 4 (2006): 471–85. http://dx.doi.org/10.1515/znb-2006-0414.

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The cyclization of a ribose-derived pentenose oxime with various halogen electrophiles showed bromine to be the most effective reagent, leading to 80% of L-lyxo/D-ribo-pyrroline N-oxides in an 84:16 diastereomeric ratio. In order to explore the scope of this facile process, several other γ,δ - unsaturated oximes were submitted to this reaction. Depending on the substitution pattern, 23 - 87%, yields of pyrroline N-oxides of were registered. With α-allyl-β -ketoester oximes the alkoxycarbonyl group proved a similar (ethoxy) or even better (t-butoxy) trapping nucleophile, leading preferentially
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9

Ali Bawa, Ramadan, and Mona Mohammed Friwan. "Synthesis and Antifungal Study of Some Acetophenone Oximes and Their Terphthaloyl Oxime Esters." Academic Journal of Chemistry, no. 410 (October 25, 2018): 96–101. http://dx.doi.org/10.32861/ajc.510.96.101.

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Acetophenone oximes 1 – 5 along with their terphthaloyl oxime esters 6 – 10 have been synthesized in moderate to good yields. Only one oxime was formed in as E/Z two isomers in a ratio of (8:1). These resulting oxime derivatives were involved in an antifungal screening against the Aspergillus niger at concentration of 30 ppm. Two commercially available antifungal agents, clorotimazole and daktarin, were employed as references at the same concentration, 30 ppm. The antifungal results for the oxime derivatives 1 – 10 showed inhibitory levels ranging from 38% to 100%, whereas the antifungal poten
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10

Spahić, Zlatan, Tomica Hrenar, and Ines Primožič. "Polytopal Rearrangement Governing Stereochemistry of Bicyclic Oxime Ether Synthesis." International Journal of Molecular Sciences 23, no. 20 (2022): 12331. http://dx.doi.org/10.3390/ijms232012331.

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In the present study, four O-substituted oximes of quinuclidin-3-one were synthesized using appropriate O-substituted hydroxylamine hydrochlorides. In order to perform these reactions in a solvent, a mixture of (E) and (Z) products was yielded. Using mechanochemical and microwave synthesis, we then obtained pure (E) oximes. In almost all cases, the conversion to oxime ethers was completed. Reactions were monitored by ATR spectroscopy and the ratios of (E) and (Z) oxime ethers were deduced from 1H NMR data. Several reactions were very rapid (1 min) with 100% conversion and stereospecificity. To
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11

Mehrez, Asma, Dalila Mtat, and Ridha Touati. "Microwave-Assisted Synthesis of Chiral Oxime Ethers." Letters in Organic Chemistry 16, no. 6 (2019): 495–500. http://dx.doi.org/10.2174/1570178615666181106125853.

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An efficient and rapid synthesis of a new class of chiral oxime ethers has been achieved via two-step reaction in which the first step is the reaction of oximes 1a-f with ethyl bromoacetate in the presence of sodium hydride to give oxime ethers 2a-f which are subsequently, in the second step, reacted with different commercially available chiral amines under microwave irradiation conditions to give compounds 3a-l in good to excellent yields. Through this method, we have observed a decrease in reaction time and excellent yields than the previously described conventional method.
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12

Abele, Edgars, and Ramona Abele. "Oximes of Nucleosides and Related Compounds: Synthesis, Reactions and Biological Activity." Current Organic Synthesis 15, no. 5 (2018): 650–65. http://dx.doi.org/10.2174/1570179415666180524112811.

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Background: Literature data on the synthesis and structure of oximes of nucleosides and related nitrogenous bases from pyrimidine and purine were reviewed. Synthesis of novel heterocyclic systems from nucleoside oximes related pyrimidine oximes was described. The biological activity of derivatives of nucleoside and nitrogenous base oximes was also reviewed. <p> Objective: The review focuses on the recent progress in the area of nucleoside oxime synthesis, reactions and biological activity. Conclusion: In summary, literature data on the synthesis and structure of oximes of nucleosides and
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13

Ali Bawa, Ramadan, and Mona Mohammed Friwan. "Synthesis of Some Acetophenone Oximes and Their Corresponding Bridged Terphthaloyl Oxime Esters." Academic Journal of Life Sciences, no. 511 (November 2, 2019): 87–92. http://dx.doi.org/10.32861/ajls.511.87.92.

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The objective of this study is to synthesize a number of oximes along with their terphthaloyl oxime esters derived from acetophenone, 4-methylacetophenone, 4-hydroxyacetophenone, 4-aminoacetophenone and 4-nitroacetophenone as a part of ongoing research. Five acetophenone oximes have been synthesized by refluxing the acetophenone derivative with a solution of hydroxylamine hydrochloride in the presence of potassium hydroxide. The corresponding acetophenone oximes were obtained as solid materials in moderate to good yields. The structures of the resulting oximes were confirmed using IR, NMR and
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14

Ren, Zhi-Hui, Mi-Na Zhao, and Zheng-Hui Guan. "CuI-catalyzed oxidative cross coupling of oximes with tetrahydrofuran: a direct access to O-tetrahydrofuran-2-yl oxime ethers." RSC Advances 6, no. 20 (2016): 16516–19. http://dx.doi.org/10.1039/c5ra27899f.

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15

Krylov, Igor B., Stanislav A. Paveliev, Alexander S. Budnikov, and Alexander O. Terent’ev. "Oxime radicals: generation, properties and application in organic synthesis." Beilstein Journal of Organic Chemistry 16 (June 5, 2020): 1234–76. http://dx.doi.org/10.3762/bjoc.16.107.

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N-Oxyl radicals (compounds with an N–O• fragment) represent one of the richest families of stable and persistent organic radicals with applications ranging from catalysis of selective oxidation processes and mechanistic studies to production of polymers, energy storage, magnetic materials design and spectroscopic studies of biological objects. Compared to other N-oxyl radicals, oxime radicals (or iminoxyl radicals) have been underestimated for a long time as useful intermediates for organic synthesis, despite the fact that their precursors, oximes, are extremely widespread and easily available
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16

Tekluu, Berihu, and Siddaiah Vidavalur. "A Facile and Efficient Protocol for the Construction of Oxime Esters from Carboxylic Acids and Evaluation of Their Antimicrobial Activities." Der Pharma Chemica 15, no. 4 (2023): 8. https://doi.org/10.5281/zenodo.13320439.

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A facile and efficient protocol for the synthesis of various structurally and electronically divergent oxime esters from carboxylic acids and oximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NMM) in 1,4-dioxane in high yields (90-97%). The synthesized compounds were assessed for their antimicrobial activities. Among the tested compounds 3d, 3j and 3p showed good antimicrobial activity.
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17

Berihu, Tekluu, and Vidavalur Siddaiah. "A Facile and Efficient Protocol for the Construction of Oxime Esters from Carboxylic Acids and Evaluation of Their Antimicrobial Activities." DER PHARMA CHEMICA 15, no. 4 (2023): 8. https://doi.org/10.4172/0975-413X.15.4.24-31.

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A facile and efficient protocol for the synthesis of various structurally and electronically divergent oxime esters from carboxylic acids and oximes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N-methylmorpholine (NMM) in 1,4-dioxane in high yields (90-97%). The synthesized compounds were assessed for their antimicrobial activities. Among the tested compounds 3d, 3j and 3p showed good antimicrobial activity.
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18

Latif, Ahmed Dhahir, Tímea Gonda, Máté Vágvölgyi, et al. "Synthesis and In Vitro Antitumor Activity of Naringenin Oxime and Oxime Ether Derivatives." International Journal of Molecular Sciences 20, no. 9 (2019): 2184. http://dx.doi.org/10.3390/ijms20092184.

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Naringenin is one of the most abundant dietary flavonoids exerting several beneficial biological activities. Synthetic modification of naringenin is of continuous interest. During this study our aim was to synthesize a compound library of oxime and oxime ether derivatives of naringenin, and to investigate their biological activities. Two oximes and five oxime ether derivatives were prepared; their structure has been elucidated by NMR and high-resolution mass spectroscopy. The antiproliferative activity of the prepared compounds was evaluated by MTT assay against human leukemia (HL-60) and gyne
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19

Surowiak, Alicja K., Stanisław Lochyński, and Daniel J. Strub. "Unsubstituted Oximes as Potential Therapeutic Agents." Symmetry 12, no. 4 (2020): 575. http://dx.doi.org/10.3390/sym12040575.

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Oximes, which are highly bioactive molecules, have versatile uses in the medical sector and have been indicated to possess biological activity. Certain oximes exist in nature in plants and animals, but they are also obtained by chemical synthesis. Oximes are known for their anti-inflammatory, antimicrobial, antioxidant and anticancer activities. Moreover, they are therapeutic agents against organophosphate (OP) poisoning. Two oximes are already commonly used in therapy. Due to these abilities, new oxime compounds have been synthesized, and their biological activity has been verified. Often, mo
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20

Surowiak, Alicja K., Stanisław Lochyński, and Daniel J. Strub. "Correction: Surowiak, A.K.; Lochyński, S.; Strub, D.J. Unsubstituted Oximes as Potential Therapeutic Agents. Symmetry 2020, 12, 575." Symmetry 12, no. 6 (2020): 1006. http://dx.doi.org/10.3390/sym12061006.

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Oximes, which are highly bioactive molecules, have versatile uses in the medical sector and have been indicated to possess biological activity. Certain oximes exist in nature in plants and animals, but they are also obtained by chemical synthesis. Oximes are known for their anti-inflammatory, antimicrobial, antioxidant and anticancer activities. Moreover, they are therapeutic agents against organophosphate (OP) poisoning. Two oximes are already commonly used in therapy. Due to these abilities, new oxime compounds have been synthesized, and their biological activity has been verified. Often, mo
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21

Naito, Takeaki. "Heterocycle synthesis via radical reactions." Pure and Applied Chemistry 80, no. 4 (2008): 717–26. http://dx.doi.org/10.1351/pac200880040717.

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A novel synthetic method for the preparation of nitrogen-containing heterocycles via the route involving domino-type radical addition/cyclization reaction of oxime ethers is described. Alkyl radical addition/cyclization of oxime ethers carrying an appropriate leaving group proceeded smoothly to form the alkylated nitrogen-containing heterocyclic compounds. Additionally, tin-mediated radical addition/cyclization/elimination (RACE) reaction of oxime ethers is newly found and successfully applied to an asymmetric total synthesis of (-)-martinellic acid.
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22

Ali Bawa, Ramadan, and Aya Ramadan Swairi. "Synthesis of Some Alicyclic Oximes and Study of the Expected Conformational Isomerism." Academic Journal of Life Sciences, no. 512 (December 5, 2019): 116–20. http://dx.doi.org/10.32861/ajls.512.116.120.

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Five alicyclic oximes 1 – 5 have been readily synthesized in moderate to good yields. These oximes were obtained through a reaction between the hydroxylamine hydrochloride and a number of alicyclic ketones (cylobutanone, cyclopentanone, cyclohexanone, cycloheptanone and cyclooctanone) under mild reaction conditions. The spectroscopic data confirmed the formation of the first four oximes 1 – 4 as single conformational isomers. However, the cyclooctanone oxime 5 was obtained as a mixture of two conformational isomers with 81% for the major and only 19% for the minor isomer. Such finding could be
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23

Krasylov, Igor V., Viktoriia Moskvina, and Volodymyr P. Khilya. "Synthetic approach to spiropyranocoumarins and their oxime derivatives." Ukr. Bioorg. Acta 2023, Vol. 18, N1 18, no. 1 (2023): 42–51. http://dx.doi.org/10.15407/bioorganica2023.01.042.

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This study explores the synthesis of a diverse series of linear (spiro)pyranocoumarins and their corresponding oximes, compounds known for their promising biological activities. Building on previous work, the authors expand the array of target compounds, adding structural features such as dimethyl groups and various cycloaliphatic rings. The novel synthetic procedure applied herein couples o-hydroxyacetyl coumarins with respective ketones via Kabbe condensation, yielding 16 derivatives, including 12 new compounds. A further step engages these (spiro)pyranocoumarins with hydroxylamine hydrochlo
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24

Kovarik, Zrinka, Hrvat Nikolina Maček, Suzana Žunec, and Maja Katalinić. "Detoxification of tabun-exposed mice by an acetylcholinesterase mutant using a novel pyridinium aldoxime." Biologia Serbica 41, no. 2 (2019): 4–8. https://doi.org/10.5281/zenodo.3532038.

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<strong>Summary. </strong>Nerve agents, such as tabun, are covalent inhibitors of acetylcholinesterase (AChE), an essential enzyme in neurotransmission whose inhibition may lead to death. Currently used therapy, consisting of an anticholinergic drug and an oxime as the reactivator of inhibited AChE is particularly ineffective in cases of tabun exposure. Thus, an optimal re-activator is still needed. Click-chemistry, utilizing Cu (I)-catalyzed azide-alkyne cycloaddition of a library of small molecule building blocks, has made possible the rapid synthesis of a variety of new oximes. Among the ne
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25

Yu, Kunru, Xiaohua Liu, Xiaobin Lin, Lili Lin, and Xiaoming Feng. "Organocatalytic dynamic kinetic resolution of azlactones to construct chiral N-acyl amino acid oxime esters." Chemical Communications 51, no. 80 (2015): 14897–900. http://dx.doi.org/10.1039/c5cc05534b.

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We have developed a chiral bisguanidinium salt catalyzed dynamic kinetic resolution of azlactones with oximes. A variety of chiral N-acyl amino acid oxime esters were generated with up to 97% ee and 99% yield. The products are useful in peptide synthesis.
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26

Narasaka, K. "Synthesis of azaheterocycles from oxime derivatives." Pure and Applied Chemistry 75, no. 1 (2003): 19–28. http://dx.doi.org/10.1351/pac200375010019.

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Electrophilic amination of Grignard reagents has been accomplished by using O-sulfonyloximes as amination reagents. Benzophenone O-sulfonyloxime derivatives react with Grignard reagents on sp2 nitrogen, yielding primary amines by successive hydrolysis of the resulting N-alkylimines. Various cyclic imines are synthesized by Pd-catalyzed reaction from olefinic oxime derivatives. That is, treatment of O-pentafluorobenzoyloximes of olefinic ketones with a catalytic amount of Pd(PPh3)4 and triethylamine affords nitrogen-containing heterocycles, such as pyrroles, pyridines, isoquinolines, spiro-imin
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27

Song, J. H., S. M. Bae, E. J. Lee, J. H. Cho, and D. I. Jung. "Formation of Benzodiazepines and Pyrazinylquinoxalines from Aromatic and Heteroaromatic Ketones via Deoximation." Asian Journal of Chemistry 32, no. 7 (2020): 1676–80. http://dx.doi.org/10.14233/ajchem.2020.22639.

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The report stated that the treatment of o-phenylenediamine with acetone dicarboxylic acid, acetone and acetophenone afforded 2,4,4-trimethyl-3H-5-hydro-1,5-benzodiazepine. However, direct reactions of o-phenylenediamine with oximes (acetone oxime, acetophenone oxime, and benzophenone oxime) as ketone equivalents did not occur. In the course of present investigations, it is found that dichloroamine-T can be an efficient reagent for the conversion of oximes into the corresponding carbonyl compounds. As a part of a research program related to the synthetic study of pharmacologically interesting b
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28

Sasaki, Kenji, Ying-Xue Zhang, Hiroshi Yamamoto, Setsuo Kashino, and Takashi Hirota. "Polycyclic N-Heterocyclic Compounds. Part 54. Ring-cleavages and Ring-closures of N-(Benzo[h]quinazolin-4-yl)amidine and its Amide Oxime Derivatives with Hydroxylamine." Journal of Chemical Research 23, no. 2 (1999): 92–93. http://dx.doi.org/10.1177/174751989902300213.

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The synthesis of abnormal cyclization products, 2-(3-alkyl(or aryl)[1,2,4]oxadiazol-5-yl)-3,4-dihydro-1-naphthylaminoformaldehyde oximes and their homologues, by the reaction of N-(benzo[ h]quinazolin-4-yl)amidine or its amide oxime derivatives with excess NH2OH · HCI are described.
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29

Pramanik, Shuvam, Sima Roy, Tapas Ghorui, Sanjib Ganguly, and Kausikisankar Pramanik. "Molecular and electronic structure of nonradical homoleptic pyridyl-azo-oxime complexes of cobalt(iii) and the azo-oxime anion radical congener: an experimental and theoretical investigation." Dalton Trans. 43, no. 14 (2014): 5317–34. http://dx.doi.org/10.1039/c3dt53460j.

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30

Ntsimango, Songeziwe, Kennedy J. Ngwira, Moira L. Bode, and Charles B. de Koning. "Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine." Beilstein Journal of Organic Chemistry 17 (September 8, 2021): 2340–47. http://dx.doi.org/10.3762/bjoc.17.152.

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Readily synthesized biphenyl-2-carbaldehyde O-acetyl oximes were exposed to UV radiation affording phenanthridines. The scope and limitations of this novel reaction were explored. For example, exposure of 2',3'-dimethoxy-[1,1'-biphenyl]-2-carbaldehyde O-acetyl oxime to UV radiation afforded 4-methoxyphenanthridine in 54% yield. This methodology was applied to the synthesis of trisphaeridine to afford the product in four linear steps in an overall yield of 6.5% from 1-bromo-2,4,5-trimethoxybenzene.
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31

Ahluwalia, Vivek, Nandini Garg, Birendra Kumar, Suresh Walia, and Om P. Sati. "Synthesis, Antifungal Activity and Structure-Activity Relationships of Vanillin Oxime-N-O-Alkanoates." Natural Product Communications 7, no. 12 (2012): 1934578X1200701. http://dx.doi.org/10.1177/1934578x1200701224.

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Vanillin oxime- N-O-alkanoates were synthesized following reaction of vanillin with hydroxylamine hydrochloride, followed by reaction of the resultant oxime with acyl chlorides. The structures of the compounds were confirmed by IR, 1H, 13C NMR and mass spectral data. The test compounds were evaluated for their in vitro antifungal activity against three phytopathogenic fungi Macrophomina phaseolina, Rhizoctonia solani and Sclerotium rolfsii by the poisoned food technique. The moderate antifungal activity of vanillin was slightly increased following its conversion to vanillin oxime, but signific
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32

Baláž, Matej, Zuzana Kudličková, Mária Vilková, Ján Imrich, Ľudmila Balážová, and Nina Daneu. "Mechanochemical Synthesis and Isomerization of N-Substituted Indole-3-carboxaldehyde Oximes †." Molecules 24, no. 18 (2019): 3347. http://dx.doi.org/10.3390/molecules24183347.

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Performing solution-phase oximation reactions with hydroxylamine hydrochloride (NH2OH·HCl) carries significant risk, especially in aqueous solutions. In the present study, four N-substituted indole-3-carboxaldehyde oximes were prepared from the corresponding aldehydes by solvent-free reaction with NH2OH·HCl and a base (NaOH or Na2CO3) using a mechanochemical approach, thus minimizing the possible risk. In all cases, the conversion to oximes was almost complete. The focus of this work is on 1-methoxyindole-3-carboxaldehyde oxime, a key intermediate in the production of indole phytoalexins with
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33

Sun, Chunzhao, Hiromichi Nishikawa, Tsubasa Inokuma, and Ken-ichi Yamada. "Diastereodivergent Construction of Octahydrophenanthridinone and Octahydrophenanthridine Cores." Molecules 30, no. 2 (2025): 371. https://doi.org/10.3390/molecules30020371.

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Diastereodivergent synthesis of octahydrophenanthridinone and octahydrophenanthridine skeletons, structural motifs often found in biologically active natural products, is described. We previously reported a total synthesis of a pancratistatin analog using novel octahydrophenanthridinone construction. In this study, we examined the generality of our method and its extension to octahydrophenanthridine formation. Conjugate addition of diarylcuprates to nitrosocyclohexenes, which were generated in situ from 2-chlorocyclohexanone oximes, provided 2-arylcyclohexanone oximes. Subsequent reduction of
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34

Gorecki, Lukas, Oksana Gerlits, Xiaotian Kong, et al. "Rational design, synthesis, and evaluation of uncharged, “smart” bis-oxime antidotes of organophosphate-inhibited human acetylcholinesterase." Journal of Biological Chemistry 295, no. 13 (2020): 4079–92. http://dx.doi.org/10.1074/jbc.ra119.012400.

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Organophosphate (OP) intoxications from nerve agent and OP pesticide exposures are managed with pyridinium aldoxime–based therapies whose success rates are currently limited. The pyridinium cation hampers uptake of OPs into the central nervous system (CNS). Furthermore, it frequently binds to aromatic residues of OP-inhibited acetylcholinesterase (AChE) in orientations that are nonproductive for AChE reactivation, and the structural diversity of OPs impedes efficient reactivation. Improvements of OP antidotes need to include much better access of AChE reactivators to the CNS and optimized orie
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35

Mirjafary, Zohreh, Morteza Abdoli, Hamid Saeidian, Sadjad Boroon, and Ali Kakanejadifard. "Oxime ethers as versatile precursors in organic synthesis: a review." RSC Advances 5, no. 97 (2015): 79361–84. http://dx.doi.org/10.1039/c5ra15299b.

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This review is a survey of the literature describing synthetic applications of oxime ethers. The cyclization and metal-catalyzed cross-coupling reactions of oxime ethers in recent years are also highlighted.
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36

Chen, Pu, Huawen Huang, Qi Tan, Xiaochen Ji, and Feng Zhao. "Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters." Molecules 28, no. 6 (2023): 2667. http://dx.doi.org/10.3390/molecules28062667.

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The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N–O bond and C–C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives
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37

Liu, Jun, Dafeng Li, Jian Li, Chunju Li, and Xueshun Jia. "Regioselective Synthesis of Functionalized Oxime Ethers." Letters in Organic Chemistry 7, no. 6 (2010): 479–82. http://dx.doi.org/10.2174/157017810791824874.

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38

Dikusar, E. A., and N. A. Zhukovskaya. "Preparative synthesis of cyclohexanone oxime esters." Russian Journal of Organic Chemistry 44, no. 9 (2008): 1389–91. http://dx.doi.org/10.1134/s1070428008090248.

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39

Ewan, Harrison S., Christine S. Muli, Steven Touba, et al. "Synthesis of sugar oxime ether surfactants." Tetrahedron Letters 55, no. 35 (2014): 4962–65. http://dx.doi.org/10.1016/j.tetlet.2014.07.036.

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40

Zhukovskaya, N. A., E. A. Dikusar, K. L. Moiseichuk, and O. G. Vyglazov. "Preparative synthesis of menthone oxime esters." Russian Journal of Applied Chemistry 79, no. 4 (2006): 634–36. http://dx.doi.org/10.1134/s1070427206040252.

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41

Liu, Si, Li-Zhi Niu, Yan-Hua Shi, Fu-Xian Wan, and Lin Jiang. "Design, Synthesis and Antifungal Activity of Novel 1-(Adamantan-1-yl) ethanone Oxime Esters." Letters in Drug Design & Discovery 17, no. 5 (2020): 526–32. http://dx.doi.org/10.2174/1570180816666190329225307.

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Background: Oxime compounds, including oxime ethers and oxime esters, possess various biological activities. Many oxime ethers have been widely used in the fields of pesticides and medicines. However, oxime ethers are rarely used in the field of pesticides. Methods: We chose the excellent fungicide pyrifenox as the lead compound, integrated pyridinyl, adamantyl and benzoyl moieties into one molecule, while also designed and synthesized ten 1- (adamantan-1-yl)ethanone oxime esters containing pyridinyl moiety. Moreover, we also evaluated their preliminary antifungal activities against S. sclerot
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42

Gao, Yanqing, Jie Song, Shibin Shang, Dan Wang, and Jian Li. "Synthesis and antibacterial activity of oxime esters from dihydrocumic acid." BioResources 7, no. 3 (2012): 4150–60. http://dx.doi.org/10.15376/biores.7.3.4150-4160.

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Dihydrocumic acid was prepared from β-pinene through oxidation and dehydration. Then, ten oxime esters from dihydrocumic acid were synthesized. Reaction conditions of the oxime esters were adjusted and their structures were characterized by IR, 1H-NMR, MS, and elemental analysis. The antibacterial activity of these newly synthesized oxime esters against Gram-negative bacteria and Gram-positive bacteria was also investigated using the inhibition zone method. The preliminary results indicated that seven compounds displayed better antibacterial activity against Gram-negative bacteria compared wit
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43

Janin, Yves, Vincent Hervin, Eloi Coutant та Glwadys Gagnot. "Synthesis of α-Amino Esters via α-Nitro or α-Oxime Esters: A Review". Synthesis 49, № 18 (2017): 4093–110. http://dx.doi.org/10.1055/s-0036-1589506.

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This review is an in-depth survey of the reported synthetic approaches for the preparation of racemic α-amino esters via the reduction of α-nitro or α-oxime ester intermediates. Accordingly, it describes the many pathways that have been designed to prepare such intermediates­. This includes synthesis starting with α-nitroacetates, dialkyl malonates, acetoacetates, diethyl oxalates as well as [2+3] or [2+4] cycloadditions using, respectively, alkyl carbonocyanidate N-oxides or alkyl 2-nitrosoacrylates. This review also contains the description of a myriad of side reactions which can occur when
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44

Wahyuningsih, Tutik Dwi. "SYNTHESIS OF NOVEL INDOLO[3,2-c]QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-c]QUINOLINE-6-CARBOXYLATE." Indonesian Journal of Chemistry 5, no. 3 (2010): 189–92. http://dx.doi.org/10.22146/ijc.21786.

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-Carboline and its derivatives are significant due to their pharmacological importance. The synthesis of indolo[3,2-c]quinolines as a benzo analog of -carboline has been carried out via an oxime ether intermediate. Reaction of 2'-glyoxylic ester with hydroxylamine hydrochloride in the presence of sodium acetate afforded the oxime acetate in 82%. It was then treated with natrium and fluoro-2,4-dinitrobenzene in ethanol to give an orange solid of oxime ether acetate which is in subsequent treatment with a base yielded a pale yellow solid of indolo[3,2-c]carboline in 43%. Keywords: -carboline,
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45

Kotipalli, Ramesh, Attunuri Nagireddy, and Maddi Sridhar Reddy. "Palladium-catalyzed cyclizative cross coupling of ynone oximes with 2-haloaryl N-acrylamides for isoxazolyl indoline bis-heterocycles." Organic & Biomolecular Chemistry 20, no. 13 (2022): 2609–14. http://dx.doi.org/10.1039/d2ob00065b.

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We demonstrated a dual-cyclizative coupling of ynone oxime ethers with acrylamides for the synthesis of isoxazolyl 2-oxindoles. The cascade is triggered by a palladium(ii)-catalyzed ynone oxime ether cyclization, and is completed by a Heck-type coupling.
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46

Peng, Ling, Chan Liu, Na Li, et al. "Direct cyclohexanone oxime synthesis via oxidation–oximization of cyclohexane with ammonium acetate." Chemical Communications 56, no. 9 (2020): 1436–39. http://dx.doi.org/10.1039/c9cc09840b.

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One-step preparation of cyclohexanone oxime from cyclohexane and ammonium acetate. 13.6% cyclohexane conversion and 51% cyclohexanone oxime selectivity are achieved. Varieties of different ammonias as readily available starting materials.
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47

Kaewsri, Wilailak, Charnsak Thongsornkleeb, Jumreang Tummatorn, and Somsak Ruchirawat. "Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles." RSC Advances 6, no. 54 (2016): 48666–75. http://dx.doi.org/10.1039/c6ra09396e.

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For the first time, 4-chloroisoxazoles are directly synthesized in moderate to excellent yields from mixtures of (E)- and (Z)-alkynyl-O-methyl oximes via (E)- to (Z)-oxime isomerization followed by chlorinative cyclization.
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48

Montenegro, Javier, José Reina, and Alicia Rioboo. "Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation." Synthesis 50, no. 04 (2018): 831–45. http://dx.doi.org/10.1055/s-0036-1591082.

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The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycos
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49

Hania, Majed M. "Synthesis and Antibacterial Activity of Some Transition Metal Complexes of Oxime, Semicarbazone and Phenylhydrazone." E-Journal of Chemistry 6, s1 (2009): S508—S514. http://dx.doi.org/10.1155/2009/204714.

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Co, Ni and Cu complexes have been prepared by reacting metal chloride with 4-chlorobenzaldehyde oxime, 4-methylbenzaldehyde oxime, 4-nitrobenzaldehyde oxime, 4-chlorobenzaldehyde semicarbazone, 4-methyl- benzaldehyde semicarbazone, 4-nitrobenzaldehyde semicarbazone, 4-chloro benzaldehyde phenylhydrazone, 4-methylbenzaldehyde phenyl hydrazone and 4-nitrobenzaldehyde phenylhydrazone and their antibacterial activity have been studied and compared with their ligands againstE. coliwhich gave significant results of activity.
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50

Bednarczyk-Cwynar, Barbara, and Piotr Ruszkowski. "Acylation of Oleanolic Acid Oximes Effectively Improves Cytotoxic Activity in In Vitro Studies." Pharmaceutics 16, no. 1 (2024): 86. http://dx.doi.org/10.3390/pharmaceutics16010086.

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(1) Background: The aim of the presented work was to obtain a set of oleanolic acid derivatives with a high level of anticancer activity and a low level of toxicity by applying an economic method. Three types of oleanolic acid derivatives were obtained: (i) derivatives of methyl oleanonate oxime, (ii) derivatives of methyl oleanonate oxime with an additional 11-oxo function, and (iii) derivatives of morpholide of oleanonic acid oxime. (2) Methods: The above oximes were acylated with aliphatic or aromatic carboxylic acid. The newly obtained compounds were subjected to ADMETox analysis and were
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