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Journal articles on the topic 'Alkoxyamine synthesis'

Author: Grafiati
Published: 25 May 2024
Last updated: 31 July 2025

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1

Romero-Ibañez, Julio, Marina A. Ortega-Rojas, Jonathan R. Valdéz-Camacho, Luis G. Hernández-Vázquez, Fernando Sartillo-Piscil, and Jaime Escalante. "Asymmetric Synthesis of trans-3-Alkoxyamino-4-Oxygenated-2-Piperidones Mediated by Transition-Metal-Free Dual C-H Oxidation and Its CAL-B-Assisted Enzymatic Resolution." Catalysts 13, no. 4 (2023): 703. http://dx.doi.org/10.3390/catal13040703.

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A general chemo-enzymatic approach to synthesize both enantioenriched trans-3-alkoxyamino-4-oxy-2-piperidones, which are important scaffold for various naturally occurring alkaloids, is reported. To this end, a selective transition-metal-free dual C−H oxidation of piperidines mediated by the TEMPO oxoammonium cation (TEMPO+) was used, followed by enzymatic resolution of the corresponding alkoxyamino-2-piperidones with Candida antarctica lipase (CAL-B), to yield the title compounds in high enantiomeric excess (ee). The absolute configuration of both enantioenriched compounds was determined usin
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2

Roy, Raj Kumar, Chloé Laure, Diane Fischer-Krauser, Laurence Charles, and Jean-François Lutz. "Convergent synthesis of digitally-encoded poly(alkoxyamine amide)s." Chemical Communications 51, no. 86 (2015): 15677–80. http://dx.doi.org/10.1039/c5cc06646h.

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3

Reyser, Thibaud, Tung H. To, Chinedu Egwu, et al. "Alkoxyamines Designed as Potential Drugs against Plasmodium and Schistosoma Parasites." Molecules 25, no. 17 (2020): 3838. http://dx.doi.org/10.3390/molecules25173838.

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Malaria and schistosomiasis are major infectious causes of morbidity and mortality in the tropical and sub-tropical areas. Due to the widespread drug resistance of the parasites, the availability of new efficient and affordable drugs for these endemic pathologies is now a critical public health issue. In this study, we report the design, the synthesis and the preliminary biological evaluation of a series of alkoxyamine derivatives as potential drugs against Plasmodium and Schistosoma parasites. The compounds (RS/SR)-2F, (RR/SS)-2F, and 8F, having IC50 values in nanomolar range against drug-res
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4

Ballard, Nicholas, Miren Aguirre, Alexandre Simula, Jose R. Leiza, Steven van Es, and José M. Asua. "High solids content nitroxide mediated miniemulsion polymerization of n-butyl methacrylate." Polymer Chemistry 8, no. 10 (2017): 1628–35. http://dx.doi.org/10.1039/c7py00067g.

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The synthesis of poly(n-butyl methacrylate) by nitroxide mediated miniemulsion polymerization is described using the alkoxyamine 3-(((2-cyanopropan-2-yl)oxy)(cyclohexyl)amino)-2,2-dimethyl-3-phenylpropanenitrile.
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5

Lukkarila, Julie L., Gordon K. Hamer, and Michael K. Georges. "Stable free radical polymerization––acrylate alkoxyamine synthesis." Tetrahedron Letters 45, no. 27 (2004): 5317–19. http://dx.doi.org/10.1016/j.tetlet.2004.04.145.

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6

He, Yan, Zhi Zheng, Yajie Liu, Jiajie Qiao, Xinying Zhang та Xuesen Fan. "Selective synthesis of β-nitrated N-heterocycles and N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted by tBuONO and oxoammonium salt". Chemical Communications 55, № 82 (2019): 12372–75. http://dx.doi.org/10.1039/c9cc05963f.

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Solvent-dependent-controlled selective synthesis of β-nitrated N-heterocycles and N-nitroso chain 2-alkoxyamine aldehydes has been successfully realized via<sup>t</sup>BuONO and oxoammonium salt promoted cascade reactions of inactivated cyclic amines.
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7

Schoening, Kai-Uwe, Stefan Hauck, Walter Fischer, and Abdel-Ilah Basbas. "Synthesis of 3-Substituted Derivatives of 2,2,6,6-Tetramethylpiperidine-N-alkoxyamine Ethers: Novel Alkoxyamine Building Blocks." Synthesis 2010, no. 22 (2010): 3873–78. http://dx.doi.org/10.1055/s-0030-1258255.

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8

Filliâtre, Marion, Pierre Voisin, Seda Seren, et al. "Pathogen Enzyme-Mediated Alkoxyamine Homolysis as a Killing Mechanism of Aspergillus fumigatus." Journal of Fungi 11, no. 7 (2025): 503. https://doi.org/10.3390/jof11070503.

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The emergence of antifungal-resistant Aspergillus fumigatus (A. fumigatus) became a serious public health concern, underscoring the need for new effective antifungal agents. Here, we present a strategy based on the in situ generation of radical species that are toxic to the pathogen. The synthesis of an alkoxyamine linked to a peptide substrate recognized by A. fumigatus-secreted dipeptidyl peptidase is described. Kinetic experiments show a stable prodrug prior to enzymatic activation. Ensuing peptide cleavage and spontaneous homolysis resulted in the generation of a stable nitroxide and a rea
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9

Leroi, Corinne, Denis Bertin, Pierre-Emmanuel Dufils, et al. "Alkoxyamine-Mediated Radical Synthesis of Indolinones and Indolines." Organic Letters 5, no. 26 (2003): 4943–45. http://dx.doi.org/10.1021/ol0358049.

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10

Tirrell, David A. "Synthesis of alkoxyamine initiators for controlled radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 36, no. 14 (1998): 2667–68. http://dx.doi.org/10.1002/(sici)1099-0518(199810)36:14<2667::aid-pola26>3.0.co;2-f.

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11

Yamaguchi, Kota, Takeshi Noda, Toshiki Tomizawa, Eriko Kanai, and Hideaki Hioki. "Solid-Phase Friedländer Synthesis Using an Alkoxyamine Linker." European Journal of Organic Chemistry 2015, no. 22 (2015): 4990–95. http://dx.doi.org/10.1002/ejoc.201500426.

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12

Chen, Senbin, Marie-Hélène Alves, Maud Save, and Laurent Billon. "Synthesis of amphiphilic diblock copolymers derived from renewable dextran by nitroxide mediated polymerization: towards hierarchically structured honeycomb porous films." Polym. Chem. 5, no. 18 (2014): 5310–19. http://dx.doi.org/10.1039/c4py00390j.

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A novel dextran-SG1 macro-alkoxyamine was designed to afford amphiphilic linear block copolymers synthesized by nitroxide mediated polymerization toward the formation of hierarchically structured bio-resourced honeycomb films.
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13

Song, Wenguang, Jian Huang, Cheng Hang, Chenyan Liu, Xuepu Wang, and Guowei Wang. "Synthesis of thermally cleavable multisegmented polystyrene by an atom transfer nitroxide radical polymerization (ATNRP) mechanism." Polymer Chemistry 6, no. 46 (2015): 8060–70. http://dx.doi.org/10.1039/c5py01493j.

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Based on the common features of well-defined NRC reaction, ATRP and NMRP mechanisms, an atom transfer nitroxide radical polymerization (ATNRP) mechanism was presented, and further used to construct multisegmented PS<sub>m</sub> embedded with multiple alkoxyamine linkages.
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14

Magee, Christopher, Aruna Earla, Jennifer Petraitis, et al. "Synthesis of fluorinated alkoxyamines and alkoxyamine-initiated nitroxide-mediated precipitation polymerizations of styrene in supercritical carbon dioxide." Polym. Chem. 5, no. 19 (2014): 5725–33. http://dx.doi.org/10.1039/c4py00757c.

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15

Bini, Davide, Francesco Nicotra, and Laura Cipolla. "Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry." Beilstein Journal of Organic Chemistry 10 (July 25, 2014): 1686–91. http://dx.doi.org/10.3762/bjoc.10.177.

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The synthesis of new dendrons of the generations 0, 1 and 2 with a double bond at the focal point and a carbonyl group at the termini has been carried out. The carbonyl group has been exploited for the multivalent conjugation to a sample saccharide by reductive amination and alkoxyamine conjugation.
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16

Fischer, Walter, Abdel-Ilah Basbas, Kai-Uwe Schoening, and Stefan Hauck. "ChemInform Abstract: Synthesis of 3-Substituted Derivatives of 2,2,6,6-Tetramethylpiperidine-N-alkoxyamine Ethers: Novel Alkoxyamine Building Blocks." ChemInform 42, no. 12 (2011): no. http://dx.doi.org/10.1002/chin.201112142.

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17

Hioki, Hideaki, Kimihito Matsushita, Takeshi Noda, et al. "Solid-phase synthesis of benzothiazoles using an alkoxyamine linker." Tetrahedron Letters 53, no. 33 (2012): 4337–42. http://dx.doi.org/10.1016/j.tetlet.2012.06.008.

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18

Moon, Bongjin, and Minhyuk Kang. "Practical synthesis of alkoxyamine initiators for living radical polymerization." Macromolecular Research 13, no. 3 (2005): 229–35. http://dx.doi.org/10.1007/bf03219057.

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19

Harrisson, Simon, Patrick Couvreur, and Julien Nicolas. "Simple and efficient copper metal-mediated synthesis of alkoxyamine initiators." Polymer Chemistry 2, no. 8 (2011): 1859. http://dx.doi.org/10.1039/c1py00131k.

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20

Bernhardt, Claire, François Stoffelbach, and Bernadette Charleux. "Synthesis and use of a new alkene-functionalized SG1-based alkoxyamine." Polym. Chem. 2, no. 1 (2011): 229–35. http://dx.doi.org/10.1039/c0py00282h.

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21

Yamaguchi, Kota, Takeshi Noda, Yusuke Higuchi, et al. "Solid-phase synthesis of benzazoles, quinazolines, and quinazolinones using an alkoxyamine linker." Tetrahedron Letters 55, no. 42 (2014): 5793–97. http://dx.doi.org/10.1016/j.tetlet.2014.08.095.

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22

Greene, Anna C., and Robert B. Grubbs. "Synthesis and evaluation of an ester-functional alkoxyamine for nitroxide-mediated polymerization." Journal of Polymer Science Part A: Polymer Chemistry 47, no. 23 (2009): 6342–52. http://dx.doi.org/10.1002/pola.23675.

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23

Aqil, M., A. Aqil, F. Ouhib, A. El Idrissi, C. Detrembleur, and C. Jérôme. "RAFT polymerization of an alkoxyamine bearing acrylate, towards a well-defined redox active polyacrylate." RSC Advances 5, no. 103 (2015): 85035–38. http://dx.doi.org/10.1039/c5ra16839b.

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24

Iwabuchi, Yoshiharu, Tetsuya Kuga, Yusuke Sasano, Masaki Tomizawa, and Masatoshi Shibuya. "Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes." Synthesis 50, no. 09 (2018): 1820–26. http://dx.doi.org/10.1055/s-0036-1591920.

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An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.
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25

Radzinski, Scott C., and Eric S. Tillman. "Trapping polystyrene radicals using nitrones: Synthesis of polymers with mid-chain alkoxyamine functionality." Polymer 52, no. 26 (2011): 6003–10. http://dx.doi.org/10.1016/j.polymer.2011.10.053.

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26

O'Bryan, Greg, Aaron Nilsen, and Rebecca Braslau. "Ketone Functionalized Nitroxides: Synthesis, Evaluation ofN-Alkoxyamine Initiators, and Derivatization of Polymer Termini." Macromolecules 40, no. 22 (2007): 7848–54. http://dx.doi.org/10.1021/ma071039s.

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27

Hill, Nicole L., and Rebecca Braslau. "Synthesis of arylethyl-functionalizedN-alkoxyamine initiators and use in nitroxide-mediated radical polymerization." Journal of Polymer Science Part A: Polymer Chemistry 45, no. 11 (2007): 2341–49. http://dx.doi.org/10.1002/pola.21993.

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28

Chen, Junyu, Junpo He, Yuefei Tao, Chengming Li, and Yuliang Yang. "Synthesis of thermosensitive gel by living free radical polymerization mediated by an alkoxyamine inimer." Polymer 51, no. 21 (2010): 4769–75. http://dx.doi.org/10.1016/j.polymer.2010.08.044.

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29

Tsimelzon, Anna, David Deamer, and Rebecca Braslau. "Synthesis and Self-Assembly of Amphiphilic Diblock Copolymers using a Fluorescently LabeledN-Alkoxyamine Initiator." Macromolecular Rapid Communications 26, no. 23 (2005): 1872–77. http://dx.doi.org/10.1002/marc.200500608.

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30

Li, Irene Q., Daniel M. Knauss, Duane B. Priddy, and Bob A. Howell. "Synthesis and reactivity of functionalized alkoxyamine initiators for nitroxide-mediated radical polymerization of styrene." Polymer International 52, no. 5 (2003): 805–12. http://dx.doi.org/10.1002/pi.1168.

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31

Chu, Ya-Fen, Yu-Min Han, Wen-Hua Chen, et al. "Synthesis of thiophene-containing acyclic alkoxyamine for nitroxide-mediated radical polymerization of acrylates and styrene." Polymer 230 (September 2021): 124062. http://dx.doi.org/10.1016/j.polymer.2021.124062.

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32

Yokomatsu, Tsutomu, Yasushi Kawase, Takehiro Yamagishi, et al. "One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex." HETEROCYCLES 78, no. 2 (2009): 463. http://dx.doi.org/10.3987/com-08-11532.

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33

Delplace, Vianney, Simon Harrisson, Hien The Ho, et al. "One-Step Synthesis of Azlactone-Functionalized SG1-Based Alkoxyamine for Nitroxide-Mediated Polymerization and Bioconjugation." Macromolecules 48, no. 7 (2015): 2087–97. http://dx.doi.org/10.1021/acs.macromol.5b00178.

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34

Vinas, Jérôme, Nelly Chagneux, Didier Gigmes, Thomas Trimaille, Arnaud Favier, and Denis Bertin. "SG1-based alkoxyamine bearing a N-succinimidyl ester: A versatile tool for advanced polymer synthesis." Polymer 49, no. 17 (2008): 3639–47. http://dx.doi.org/10.1016/j.polymer.2008.06.017.

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35

Denizligil, Selçuk, and Yusuf Yagci. "Synthesis of polytetrahydrofuran with alkoxyamine end-groups and its use in block copolymerization with styrene." Designed Monomers and Polymers 1, no. 1 (1998): 121–28. http://dx.doi.org/10.1163/156855598x00170.

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36

Dao, Julian, Didier Benoit, and Craig J. Hawker. "A versatile and efficient synthesis of alkoxyamine LFR initiators via manganese based asymmetric epoxidation catalysts." Journal of Polymer Science Part A: Polymer Chemistry 36, no. 12 (1998): 2161–67. http://dx.doi.org/10.1002/(sici)1099-0518(19980915)36:12<2161::aid-pola24>3.0.co;2-3.

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37

Matsushita, Kimihito, Chieko Okamoto, Mayumi Yoshimoto, et al. "Novel Alkoxyamine Linker to Load Ketones for Solid-Phase Synthesis: Application of the Synthesis of 1,4-Benzodiazepine-2-ones." Journal of Combinatorial Chemistry 12, no. 3 (2010): 311–14. http://dx.doi.org/10.1021/cc9001795.

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38

Harnden, M. R., R. J. Ashton, M. R. Boyd, L. J. Jennings, D. Sutton, and P. G. Wyatt. "Synthesis, Oral Bioavailability and in vivo Activity of Acetal Derivatives of the Selective Antiherpesvirus Agent 9-(3-hydroxypropoxy) Guanine (BRL 44385)." Antiviral Chemistry and Chemotherapy 5, no. 3 (1994): 147–54. http://dx.doi.org/10.1177/095632029400500302.

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Acyclic acetal derivatives of the selective antiherpesvirus agent 9-(3-hydroxypropoxy) guanine (BRL44385) and of its 2-aminopurine congener (BRL46720) have been prepared and evaluated in mice for oral delivery of BRL 44385. Guanine derivatives (6 a-c) were prepared via Mitsunobu condensation of an alcohol with a 9-hydroxy-6-methoxypurine (Harnden and Wyatt, 1990). Synthesis of derivatives of 2-aminopurine (10 a-d) was achieved by hydrogenolysis of 9-alkoxy-6-chloropurines, which were obtained either by reaction of an alkoxyamine with 4,6-dichloro-2,5-diformamidopyrimidine and subsequent ring c
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39

Miura, Yozo, Kenichi Hirota, Hiroaki Moto, and Bunichiro Yamada. "High-Yield Synthesis of Functionalized Alkoxyamine Initiators and Approach to Well-Controlled Block Copolymers Using Them." Macromolecules 32, no. 25 (1999): 8356–62. http://dx.doi.org/10.1021/ma9907542.

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40

Wang, Xuepu, Jian Huang, Lingdi Chen, Yujie Liu, and Guowei Wang. "Synthesis of Thermal Degradable Poly(alkoxyamine) through a Novel Nitroxide Radical Coupling Step Growth Polymerization Mechanism." Macromolecules 47, no. 22 (2014): 7812–22. http://dx.doi.org/10.1021/ma501613x.

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41

Bothe, Marc, and Gudrun Schmidt-Naake. "An Improved Catalytic Method for Alkoxyamine Synthesis – Functionalized and Biradical Initiators for Nitroxide-Mediated Radical Polymerization." Macromolecular Rapid Communications 24, no. 10 (2003): 609–13. http://dx.doi.org/10.1002/marc.200350002.

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42

Jayasekara, P. Suresh, and Kenneth A. Jacobson. "Rapid Synthesis of Alkoxyamine Hydrochloride Derivatives from Alkyl Bromide and N,N′-Di-tert-butoxycarbonylhydroxylamine [(Boc)2NOH]." Synthetic Communications 44, no. 16 (2014): 2344–47. http://dx.doi.org/10.1080/00397911.2014.895014.

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43

Higaki, Yuji, Hideyuki Otsuka, and Atsushi Takahara. "Synthesis of well-defined poly(styrene)-b-poly(p-tert-butoxystyrene) multiblock copolymer from poly(alkoxyamine) macroinitiator." Polymer 44, no. 23 (2003): 7095–101. http://dx.doi.org/10.1016/j.polymer.2003.09.002.

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44

Wang, Binglin, Jiaxin Li, Xuejun Lai, Hongqiang Li, Yishen Chen, and Xingrong Zeng. "Synthesis of a novel N ‐alkoxyamine containing macromolecular intumescent flame retardant and its synergism in flame‐retarding polypropylene." Polymers for Advanced Technologies 32, no. 6 (2021): 2452–64. http://dx.doi.org/10.1002/pat.5275.

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45

Abraham, Sinoj, Jae Ho Choi, Jin Kyu Lee, Chang-Sik Ha, and Il Kim. "Synthesis of star-like random copolymers from resorcinarene-based octa-functional alkoxyamine initiatorvia nitroxide mediated free radical polymerization." Macromolecular Research 15, no. 4 (2007): 324–29. http://dx.doi.org/10.1007/bf03218794.

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46

Abraham, Sinoj, Jae Ho Choi, Chang-Sik Ha, and Il Kim. "Synthesis of star polymers via nitroxide mediated free-radical polymerization: A “core-first” approach using resorcinarene-based alkoxyamine initiators." Journal of Polymer Science Part A: Polymer Chemistry 45, no. 23 (2007): 5559–72. http://dx.doi.org/10.1002/pola.22302.

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47

Flakus, Silke, and Gudrun Schmidt-Naake. "Synthesis of Graft Copolymers by Nitroxide Mediated Radical Polymerization of Styrene andn-Butylacrylate Using Alkoxyamine-Functionalized Copolymers as Macroinitiators." Macromolecular Symposia 275-276, no. 1 (2009): 43–51. http://dx.doi.org/10.1002/masy.200950105.

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48

Datsyuk, Vitaliy, Laurent Billon, Christelle Guerret-Piécourt, et al. "In Situ Nitroxide-Mediated Polymerized Poly(acrylic acid) as a Stabilizer/Compatibilizer Carbon Nanotube/Polymer Composites." Journal of Nanomaterials 2007 (2007): 1–12. http://dx.doi.org/10.1155/2007/74769.

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Carbon nanotube (CNT) polymer composites were synthesized via in situ nitroxide-mediated diblock copolymerization. Poly(acrylic acid) (PAA) was chosen as a first block to obtain a precomposite CNT-PAA which is readily dispersible in various solvents including water. The immobilization of the stable poly(acrylic acid) alkoxyamine functionality on the nanotube surface occurs during the synthesis of the first block without CNT prior treatment. The living character of this block is established by spectroscopic methods and the nature of the CNT/PAA interaction is discussed. This living first block
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49

Gigmes, Didier, Pierre-Emmanuel Dufils, David Glé, Denis Bertin, Catherine Lefay, and Yohann Guillaneuf. "Intermolecular radical 1,2-addition of the BlocBuilder MA alkoxyamine onto activated olefins: a versatile tool for the synthesis of complex macromolecular architecture." Polymer Chemistry 2, no. 8 (2011): 1624. http://dx.doi.org/10.1039/c1py00057h.

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50

Krause, T., W. D. Habicher, M. Messerschmidt, and B. I. Voit. "A novel method for the synthesis of alkoxyamine initiators for nitroxide-mediated radical polymerization using Mn(OAc)3 as electron-transfer reagent." Designed Monomers and Polymers 7, no. 4 (2004): 391–97. http://dx.doi.org/10.1163/1568555041475275.

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