Journal articles: 'Oxime ethers'

1

Shan, Z., Y. Chu, D. Liu, and N. Sun. "Spiroborate Ether Mediated Enantioselective Reduction of Oxime Ethers." Synfacts 2006, no. 7 (June 2006): 0691. http://dx.doi.org/10.1055/s-2006-941859.

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2

Zhang, Jia-Yuan, Jinglin Hu, Xiao-Xuan Li, Wei-Ke Tang, and Yi-Si Feng. "Metal-Free Transformation of Sulfonyl Oxime Ethers with Amines to Oxime Ethers." Journal of Organic Chemistry 86, no. 18 (September 2, 2021): 12676–82. http://dx.doi.org/10.1021/acs.joc.1c01197.

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3

Mehrez, Asma, Dalila Mtat, and Ridha Touati. "Microwave-Assisted Synthesis of Chiral Oxime Ethers." Letters in Organic Chemistry 16, no. 6 (April 23, 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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4

MEIER, H., K. SAUL, R. MENGEL, and H. P. NIEDERMANN. "ChemInform Abstract: Cycloaddition of Benzothiete to Oximes, Oxime Ethers, and Oxime Esters." ChemInform 22, no. 46 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199146227.

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5

Bartlett, Paul A., Kevin L. McLaren, and Pauline C. Ting. "Radical cyclization of oxime ethers." Journal of the American Chemical Society 110, no. 5 (March 1988): 1633–34. http://dx.doi.org/10.1021/ja00213a052.

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6

Wimmer, Zdenêk, David Šaman, Jorga Smolíková, and Miroslav Romaňuk. "Oxime ethers as potential juvenoids." Liebigs Annalen der Chemie 1988, no. 11 (November 15, 1988): 1091–94. http://dx.doi.org/10.1002/jlac.198819881114.

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7

BRAIN, EDWARD G., ANDREW K. FORREST, ERIC HUNT, CHRISTINE SHILLINGFORD, and JENNIFER M. WILSON. "Erythromycin a oxime 11,12-carbonate and its oxime ethers." Journal of Antibiotics 42, no. 12 (1989): 1817–22. http://dx.doi.org/10.7164/antibiotics.42.1817.

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8

Diaz-Velandia, John, Natalia Durán-Díaz, Jorge Robles-Camargo, and Alix Elena Loaiza. "Síntesis y evaluación “in vitro” de la actividad antifúngica de oximas, éteres de oxima e isoxazoles." Universitas Scientiarum 16, no. 3 (November 1, 2011): 294. http://dx.doi.org/10.11144/javeriana.sc16-3.saiv.

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Objective. To synthesize and carry out a preliminary evaluation of the in vitro antifungal activity of oximes, oxime ethers and isoxazoles. Materials and methods. Oximes were synthesized from aldehydes or ketones with NH2OH.HCl and K2CO3. Oxime ethers were prepared by alkylation of oximes with propargyl bromide or 2-bromobenzyl bromide, using NaOH as base and acetone as solvent. The isoxazoles were obtained by 1,3-dipolar cycloadditions using ceric ammonium nitrate (CAN), chloramine T (CAT) and NaOCl. Products were identified or characterized using nuclear magnetic resonance (NMR) and mass spectrometry (MS). Radial growth inhibition assays against Aspergillus niger and Fusarium roseum were carried out. Results. Five oximes, seven oxime ethers, four of them new, and four new isoxazoles were obtained. The assessed substances exhibited antifungal activity in amounts of 1,5 mg and 3,0 mg. Conclusions. Although 1,3-dipolar cycloadditions allowed to obtain the desired isoxazoles, this methodology produced a wide variety of side products that reduced yields and made difficult the purification of the target products. Four of the tested compounds showed inhibition percentages greater than 80%. Key words: oximes, oxime ethers, isoxazoles, antifungal activity.

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9

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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10

Naito, Takeaki. "Heterocycle synthesis via radical reactions." Pure and Applied Chemistry 80, no. 4 (January 1, 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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11

Dieter, R. Karl, and Ravindra Datar. "1,2-Nucleophilic additions of organolithium reagents to chiral oxime ethers." Canadian Journal of Chemistry 71, no. 6 (June 1, 1993): 814–23. http://dx.doi.org/10.1139/v93-108.

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Chiral oxime ethers are readily prepared from chiral alkoxyamines derived from ephedrine and norephedrine. These chiral oxime ethers of isobutyraldehyde and benzaldehyde undergo 1,2-nucleophilic addition reactions with alkyllithium reagents (n-BuLi, PhLi and n-BuLi, tert-butyllithium, respectively) to afford the chiral alkoxyamines with a diastereomeric excess of 64–88%. Reduction of the alkoxyamines with LiAlH4 gave the corresponding chiral amines. The diastereoselectivity of the reaction appears to directly mirror the E:Z ratio of the starting oxime ethers.

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12

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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13

Liu, Jun, Dafeng Li, Jian Li, Chunju Li, and Xueshun Jia. "Regioselective Synthesis of Functionalized Oxime Ethers." Letters in Organic Chemistry 7, no. 6 (September 1, 2010): 479–82. http://dx.doi.org/10.2174/157017810791824874.

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14

Kawamura, Yasuhiko, Takahiro Abe, and Masao Tsukayama. "One-Way and Two-Way Geometrical Isomerizations of 1, 1-Diarylketone Oxime O-Methyl Ethers Induced by Photosensitized Electron Transfer." International Journal of Modern Physics B 17, no. 08n09 (April 10, 2003): 1487–91. http://dx.doi.org/10.1142/s0217979203019204.

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Under an oxygen atmosphere, the E and Z isomer ratio of N-methoxy-4-methoxyphenyl-4'-methylphenylmethanimine (one of the title compounds; initially, ⌈E⌉/⌈Z⌉ = 1/1) reached to 4/96 upon irradiation (> 360 nm) of 9, 10-dicyanoanthracene (DCA) as a photosensitizer in acetonitrile. Key intermediate is presumed to be a putative distonic radical cation which is a unique one having a spatially separate radical and ionic centers on the molecular framework. The whole scenario of the reaction was supported by molecular orbital calculations. An excited singlet state of DCA generated by light absorption was quenched by oxime ethers to give the DCA anion radical and radical cations of E- and Z-oxime ethers. Then the subsequent single electron transfer from the DCA anion radical to molecular oxygen generates superoxide anion radical, which reacted with distonic radical cations of E- and Z-oxime ethers bya ⌈supra + antara⌉ manner. Geometry selection occurs at a stage of just making a new bond between nitrogen and oxygen terminals in the ensuing peroxyaminy1-1,4-diradical. The final oxime ether is afforded by releasing molecular oxygen without successful single bond formation. Instead, ring closure to azadioxetane gives rise to formation of byproducts, benzophenones and methyl nitrite, by decomposion of it in a metathesis fashion.

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15

Zeng, Xiaobao, Xin Wang, Yanan Zhang, Li Zhu, and Yu Zhao. "A silver-catalyzed radical ring-opening reaction of cyclopropanols with sulfonyl oxime ethers." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3734–39. http://dx.doi.org/10.1039/d0ob00055h.

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A simple and efficient method for the radical ring-opening reaction of cyclopropanols with sulfonyl oxime ethers catalyzed by AgNO₃ is developed, affording γ-keto oxime ethers in moderate to good yields.

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16

Sun, Baozhen, Shuang Liu, Mengru Zhang, Jinbo Zhao, and Qian Zhang. "Pd-Catalyzed carboannulation of γ,δ-alkenyl oximes: efficient access to 5-membered cyclic nitrones and dihydroazines." Organic Chemistry Frontiers 6, no. 3 (2019): 388–92. http://dx.doi.org/10.1039/c8qo01076e.

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17

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 (May 18, 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. sclerotiorum and B. cinerea. Results: The target compounds were characterized by NMR, IR and HRMS. The preliminary bioactivity test showed that they exhibited some antifungal activity to S. sclerotiorum and B. cinerea, and EC50 values were in the range of 14.16-32.97 and 27.60-52.82 μg/mL, respectively. Conclusion: Some target compounds such as 3d, 3e, 3h and 3i, exhibited moderate activities against S. sclerotiorum, with EC50 values of 14.16-18.18 μg/mL.

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18

Wu, Fang Fang, Yu Rong Song, Jiao Yu Zhang, Lei Chen, and Jun Zhi Wang. "Synthesis and In Vitro Anti-Ulcer Effect of Bisabolangelone Oxime Ether Derivatives." Advanced Materials Research 781-784 (September 2013): 1122–25. http://dx.doi.org/10.4028/www.scientific.net/amr.781-784.1122.

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Four bisabolangelone oxime ether derivatives were synthesized and separated as potential anti-ulcer agents. Their structures were characterized by NMR, IR and ESI-MS. Preliminarily H+/K+-ATPase activity evaluation indicated that all the target oxime ethers exhibited the better H+/K+-ATPase inhibitory activities than the commercial omeprazole with the IC50of 17~46 μM. These compounds might be used as potential anti-ulcer agents in the treatment of acid-related diseases.

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19

Kim, Sundae, Nurul Ain Bte Kamaldin, Sol Kang, and Sunggak Kim. "Facile nucleophilic substitution of sulfonyl oxime ethers: an easy access to oxime ethers, carbonyl compounds and amines." Chemical Communications 46, no. 41 (2010): 7822. http://dx.doi.org/10.1039/c0cc02081h.

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20

Bhattacharyya, Aditya, Subhomoy Das, Navya Chauhan, Pronay K. Biswas, and Manas K. Ghorai. "Facile Synthesis of Oxime Amino Ethers via Lewis Acid Catalyzed SN2-Type Ring Opening of Activated Aziridines with Aryl Aldehyde Oximes." Synlett 31, no. 07 (March 2, 2020): 708–12. http://dx.doi.org/10.1055/s-0039-1691596.

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A simple strategy to access a wide range of substituted oxime amino ethers in good to high yields via Lewis acid catalyzed SN2-type ring opening of activated aziridines with aryl aldehyde oximes is reported.

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21

Tavakol, Hossein, Saedeh Zakery, and Akbar Heydari. "Chemoselective addition of organometallics to oxime ethers." Journal of Organometallic Chemistry 692, no. 10 (April 2007): 1924–27. http://dx.doi.org/10.1016/j.jorganchem.2006.12.038.

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22

OHSUMI, Tadashi, Makoto HATAKOSHI, Hirosi KISIDA, Noritada MATSUO, Isamu NAKAYAMA, and Nobushige ITAYA. "Oxime ethers: New potent insect growth regulators." Agricultural and Biological Chemistry 49, no. 11 (1985): 3197–202. http://dx.doi.org/10.1271/bbb1961.49.3197.

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23

Hatem, J., C. Henriet-Bernard, J. Grimaldi, and R. Maurin. "Radical cyclization of β-allenic oxime ethers." Tetrahedron Letters 33, no. 8 (February 1992): 1057–58. http://dx.doi.org/10.1016/s0040-4039(00)91859-8.

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24

Ohsumi, Tadashi, Makoto Hatakoshi, Hirosi Kisida, Noritada Matsuo, Isamu Nakayama, and Nobushige Itaya. "Oxime Ethers: New Potent Insect Growth Regulators." Agricultural and Biological Chemistry 49, no. 11 (November 1985): 3197–202. http://dx.doi.org/10.1080/00021369.1985.10867257.

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25

Rodriques, Karen E., Anwer Basha, James B. Summers, and Dee W. Brooks. "Addition of aryllithium compounds to oxime ethers." Tetrahedron Letters 29, no. 28 (January 1988): 3455–58. http://dx.doi.org/10.1016/0040-4039(88)85188-8.

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26

Zhou, Fei, Can Li, Meng Li, Yangbin Jin, Huanfeng Jiang, Yingjun Zhang, and Wanqing Wu. "Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans via palladium-catalyzed cascade cyclization of alkenyl ethers." Chemical Communications 57, no. 39 (2021): 4799–802. http://dx.doi.org/10.1039/d1cc00709b.

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27

Kim, Sundae, Nurul Ain Bte Kamaldin, Sol Kang, and Sunggak Kim. "ChemInform Abstract: Facile Nucleophilic Substitution of Sulfonyl Oxime Ethers: An Easy Access to Oxime Ethers, Carbonyl Compounds and Amines." ChemInform 42, no. 9 (February 3, 2011): no. http://dx.doi.org/10.1002/chin.201109025.

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28

Choi, Subin, Sujin Ha, and Cheol-Min Park. "α-Diazo oxime ethers for N-heterocycle synthesis." Chemical Communications 53, no. 45 (2017): 6054–64. http://dx.doi.org/10.1039/c7cc02650a.

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29

Anand, Naveen, Nathan A. Owston, Alexandra J. Parker, Paul A. Slatford, and Jonathan M. J. Williams. "Ruthenium-catalysed conversion of oxime ethers into nitriles." Tetrahedron Letters 48, no. 44 (October 2007): 7761–63. http://dx.doi.org/10.1016/j.tetlet.2007.09.028.

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30

Rudolf Pfaendler, Hans, and Helmut Meffert. "Oxime Ethers as Structure Analogs of Clavulanic Acid." HETEROCYCLES 47, no. 2 (1998): 1013. http://dx.doi.org/10.3987/com-97-s(n)75.

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31

Bhattarai, Bijay T., Sarju Adhikari, Elizabeth A. Kimball, Jane N. Moore, Kevin H. Shaughnessy, Timothy S. Snowden, Frank R. Fronczek, and Debra D. Dolliver. "Palladium-catalyzed ortho-halogenation of diaryl oxime ethers." Tetrahedron Letters 55, no. 34 (August 2014): 4801–6. http://dx.doi.org/10.1016/j.tetlet.2014.06.080.

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32

Fréneau, Maxime, Pascal de Sainte Claire, Norbert Hoffmann, Jean-Pierre Vors, Julie Geist, Michel Euvrard, and Claire Richard. "Phototransformation of tetrazoline oxime ethers: photoisomerization vs. photodegradation." RSC Advances 6, no. 7 (2016): 5512–22. http://dx.doi.org/10.1039/c5ra24936h.

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33

Sharma, Kamlesh, Shivani B. Mishra, and Ajay K. Mishra. "Synthesis and Mechanistic Study of Steroidal Oxime Ethers." Helvetica Chimica Acta 94, no. 12 (December 2011): 2256–63. http://dx.doi.org/10.1002/hlca.201100232.

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34

Martin, D. "Preparation of ?-Hydroxyalkyl Oxime Ethers and ?-Hydroxyalkyl Hydrazones." Journal f�r Praktische Chemie/Chemiker-Zeitung 337, no. 1 (1995): 599–600. http://dx.doi.org/10.1002/prac.199533701126.

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35

Ortiz-Marciales, M., X. Huang, K. Huang, V. Stepanenko, F. Merced, A. Ayala, W. Correa, and M. De Jesús. "Spiroborate-Catalyzed Asymmetric Borane Reduction of Oxime Ethers." Synfacts 2007, no. 7 (July 2007): 0722. http://dx.doi.org/10.1055/s-2007-968669.

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36

Akcamur, Yunus, and Gert Kollenz. "A SIMPLE SYNTHESIS OF SOME NOVEL OXIME ETHERS." Organic Preparations and Procedures International 19, no. 1 (February 1987): 52–56. http://dx.doi.org/10.1080/00304948709354871.

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37

Miyabe, Hideto, Yoshiji Takemoto, and Akira Toyoda. "Enantioselective Cascade Radical Addition-Cyclization of Oxime Ethers." Synlett 2007, no. 12 (July 2007): 1885–88. http://dx.doi.org/10.1055/s-2007-984530.

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38

Park, Hyun-Ja, Kyung Lee, Su-Jin Park, Bangle Ahn, Jong-Cheol Lee, HeeYeong Cho, and Kee-In Lee. "Identification of antitumor activity of pyrazole oxime ethers." Bioorganic & Medicinal Chemistry Letters 15, no. 13 (July 2005): 3307–12. http://dx.doi.org/10.1016/j.bmcl.2005.03.082.

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39

van den Hoogenband, Adri, Jan H. van Maarseveen, Andrew C. McCreary, Arie T. Mulder, Guus J. M. van Scharrenburg, Herman H. van Stuivenberg, Theo J. J. Zethof, Barbara Zijta, and Wouter I. Iwema Bakker. "Piperazinyl oxime ethers as NK-1 receptor antagonists." Bioorganic & Medicinal Chemistry Letters 16, no. 4 (February 2006): 1045–48. http://dx.doi.org/10.1016/j.bmcl.2005.10.077.

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40

Glaser, Rainer, and A. Streitwieser. "Theoretical study of structure and reactions of metalated oximes and oxime ethers." Pure and Applied Chemistry 60, no. 2 (January 1, 1988): 195–204. http://dx.doi.org/10.1351/pac198860020195.

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41

Fréneau, Maxime, Norbert Hoffmann, Jean-Pierre Vors, Pierre Genix, Claire Richard, and Pascal de Sainte Claire. "Phototransformation of tetrazoline oxime ethers – part 2: theoretical investigation." RSC Advances 6, no. 68 (2016): 63965–72. http://dx.doi.org/10.1039/c6ra07712a.

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42

Mirjafary, Zohreh, Morteza Abdoli, Hamid Saeidian, Ali Kakanejadifard, and S. Morteza F. Farnia. "Review of the synthesis of acyclic and cyclic oxime ethers." RSC Advances 6, no. 21 (2016): 17740–58. http://dx.doi.org/10.1039/c5ra25591k.

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43

Peng, Jing, Chao Chen, and Chanjuan Xi. "β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)–H bonds using a palladium catalyst." Chem. Sci. 7, no. 2 (2016): 1383–87. http://dx.doi.org/10.1039/c5sc03903g.

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44

Kim, Sangmo, Kyoung-Chan Lim, Sunggak Kim, and Ilhyong Ryu. "Tin-Free Radical Carbonylation: Synthesis of Acylated Oxime Ethers Using Alkyl Allyl Sulfone Precursors, Carbon Monoxide, and Phenylsulfonyl Oxime Ether." Advanced Synthesis & Catalysis 349, no. 4-5 (March 5, 2007): 527–30. http://dx.doi.org/10.1002/adsc.200600500.

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45

Miyabe, Hideto, Okiko Miyata, and Takeaki Naito. "Heterocycle Synthesis via Radical Addition-Cyclization of Oxime Ethers." Journal of Synthetic Organic Chemistry, Japan 60, no. 11 (2002): 1087–94. http://dx.doi.org/10.5059/yukigoseikyokaishi.60.1087.

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46

Miyabe, Hideto, Hirotaka Tanaka, and Takeaki Naito. "Triethylborane-induced solid-phase radical cyclization of oxime ethers." Tetrahedron Letters 40, no. 48 (November 1999): 8387–90. http://dx.doi.org/10.1016/s0040-4039(99)01788-8.

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47

El Kaim, Laurent, Ariane Gacon, and Aymeric Perroux. "Thiophenol promoted radical cyclisation of hydrazones and oxime ethers." Tetrahedron Letters 39, no. 5-6 (January 1998): 371–74. http://dx.doi.org/10.1016/s0040-4039(97)10592-5.

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48

Enholm, Eric J., J. A. Burroff, and Luz M. Jaramillo. "Free radical cyclizations of terminal alkynes with oxime ethers." Tetrahedron Letters 31, no. 26 (1990): 3727–30. http://dx.doi.org/10.1016/s0040-4039(00)97455-0.

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49

HATEM, J., C. HENRIET-BERNARD, J. GRIMALDI, and R. MAURIN. "ChemInform Abstract: Radical Cyclization of β-Allenic Oxime Ethers." ChemInform 23, no. 37 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199237133.

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50

Wimmer, Zdenêk, Soňa Vašíčková, David Šaman, and Miroslav Romaňuk. "Oxime ethers as potential juvenoids: Synthesis of optical isomers." Liebigs Annalen der Chemie 1990, no. 9 (September 12, 1990): 847–52. http://dx.doi.org/10.1002/jlac.1990199001159.

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Journal articles on the topic 'Oxime ethers'

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