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Journal articles on the topic 'O-hydroxylamines'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Khomutov, R. M., and A. R. Khomutov. "Mercurated o-substituted hydroxylamines." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 11 (1985): 2454–55. http://dx.doi.org/10.1007/bf00956834.

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2

Spooren, Anita AMG, and Chris TA Evelo. "Only the glutathione dependent antioxidant enzymes are inhibited by haematotoxic hydroxylamines." Human & Experimental Toxicology 17, no. 10 (1998): 554–59. http://dx.doi.org/10.1177/096032719801701005.

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Hydroxylamine and some of its derivatives are known to cause oxidative effects both in vitro and in vivo.Inthe current study we investigated the effects of hydroxyla-mines on the enzymatic antioxidant defense system in human erythrocytes. The activity of catalase and super-oxide dismutase was not significantly influenced by any of the hydroxylamines tested. However, the activity of glutathione peroxidase (GPX) and glutathione S-transferase (GST) was strongly inhibited by hydroxylamine and its O-derivatives (O-methyl and O-ethyl hydroxylamine). GPX was also inhibited by two N-derivatives of hyd

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3

Johnson, Alyssa L., Nathan Duncan, and Michael D. Mosher. "O-Benzyl-N-(9-acridinyl)hydroxylamines." Arkivoc 2018, no. 4 (2018): 139–48. http://dx.doi.org/10.24820/ark.5550190.p010.472.

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4

Clemens, Andrea, Richard P. Kreher, and Johannes Preut. "Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXX. 3-Hydroximino-1-alkyl(aryl)-isoindoline und 3-Hydroxylamino-1-alkyl(aryl)-1Hisoindole - Modellverbindungen für Struktur- und Reaktivitätsuntersuchungen - / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXX. 3-Hydroximino-1-alkyl(aryl)-isoindolines and 3-Hydroxylamino-1-alkyl(aryl)-1Hisoindoles - Model Compounds for Investigations of Structure and Reactivity -." Zeitschrift für Naturforschung B 51, no. 12 (1996): 1791–810. http://dx.doi.org/10.1515/znb-1996-1218.

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3-Hydroximino-isoindolines and 3-hydroxylamino-1 H-isoindoles with substituents at the five membered ring have been prepared by condensation of substituted 3-alkoxy-1 H-isoindoles with hydroxylamine and O-/N -substituted hydroxylamines. Constitution and configuration of semi-cyclic amidoximes were derived from spectroscopic investigations and deduced on the basis of orientating chemical transformations. These results have been established by a crystal structure determination of a representative 3-hydroximino-isoindoline.

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5

Fioravanti, Stefania, Lucio Pellacani, and Paolo A. Tardella. "O-Arylsulfonyl hydroxylamines via a decarboxylative rearrangement." Tetrahedron 65, no. 29-30 (2009): 5747–51. http://dx.doi.org/10.1016/j.tet.2009.05.016.

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6

Matassini, Camilla, Andrea Goti, Camilla Parmeggiani, and Francesca Cardona. "On the Oxidation of Hydroxylamines with o-Iodoxybenzoic Acid (IBX)." Synthesis 49, no. 13 (2017): 2890–900. http://dx.doi.org/10.1055/s-0036-1588457.

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o-Iodoxybenzoic acid (IBX) is confirmed as a powerful tool for the oxidation of hydroxylamines. The synthetic route is demonstrated as efficient and user friendly, and is exploited on various carbohydrate-derived N,N-disubstituted hydroxylamines (cyclic, acyclic, and functionalized ones), affording the corresponding nitrones in good yields and regioselectivity. N-Monosubstituted hydroxylamines revealed an interesting divergent behavior depending on the reaction conditions. While IBX oxidation in dimethyl sulfoxide at 45 °C furnished oximes as reported, the oxidation in dichloromethane at room

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7

Dhanju, Sandeep, and David Crich. "Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N,N-Disubstituted Hydroxylamines." Organic Letters 18, no. 8 (2016): 1820–23. http://dx.doi.org/10.1021/acs.orglett.6b00556.

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8

Aurich, Hans Günter, Christian Gentes та Ulrich Sievers. "Darstellung chiraler heterocyclischer β-Aminosäureester / Preparation of Chiral Heterocyclic Esters of β-Amino Acids". Zeitschrift für Naturforschung B 54, № 4 (1999): 519–31. http://dx.doi.org/10.1515/znb-1999-0416.

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Chiral β-amino alcohols were successively prone to N-benzylation, O-allylation and oxidation of the resulting benzylamino group to give nitrones 3 which on hydrolysis afforded chiral hydroxylamines HO-NH-CH(R)-CH2-O-CH2-CH=CH2 ((S)-4: R = Me, Bn, iPr. (R)-4: R = Et). Swern oxidation of methyl 2,2-dimethyl-3-hydroxypropionate (16) and treatment of the resulting aldehyde 17 with hydroxylamines (S)-4b (R = Bn) or (R)-4d (R = Et) provided nitrones 18 that underwent an intramolecular 1,3-dipolar cycloaddition on heating yielding the bicyclic β-amino-acid esters 19b and ent-19d, respectively.Reducti

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9

Bates, Roderick W., and Kanicha Sa-Ei. "O-Alkenyl Hydroxylamines: A New Concept for Cyclofunctionalization." Organic Letters 4, no. 24 (2002): 4225–27. http://dx.doi.org/10.1021/ol026701d.

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10

Defoin, Albert, Sébastien Albrecht, and Céline Tarnus. "Simple Preparation of O-Substituted Hydroxylamines from Alcohols." Synthesis 2006, no. 10 (2006): 1635–38. http://dx.doi.org/10.1055/s-2006-926440.

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11

Egart, Boris, Dieter Lentz, and Constantin Czekelius. "Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines." Journal of Organic Chemistry 78, no. 6 (2013): 2490–99. http://dx.doi.org/10.1021/jo3026725.

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12

Demuth, H. U., R. Baumgrass, C. Schaper, G. Fischer, and A. Barth. "Dipeptidylpeptidase Iv - Inactivation with N-Peptidyl-O-Aroyl Hydroxylamines." Journal of Enzyme Inhibition 2, no. 2 (1988): 129–42. http://dx.doi.org/10.3109/14756368809040718.

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13

Nazarian, Zohreh, and Craig M. Forsyth. "A Cascade Process of Hydroxamates Renders 1,6-Dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones." Synthesis 53, no. 12 (2021): 2081–91. http://dx.doi.org/10.1055/s-0040-1706660.

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AbstractA cascade route to 1,6-dioxa-3,9-diazaspiro[4.4]nonane-2,8-diones from N,O-diacyl hydroxylamines consisting of a two-step procedure is described. The key transformation is a [3,3]-sigmatropic rearrangement of N,O-diacyl hydroxylamines promoted by formation of a silylketenaminal followed by an intramolecular cyclization and a final spirocyclization. The optimum reaction conditions employ a one-fold excess of each reagent and are utilized to prepare a range of structurally diverse examples of this class of compound.

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14

Noda, Hidetoshi, and Jeffrey W. Bode. "Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines." Chem. Sci. 5, no. 11 (2014): 4328–32. http://dx.doi.org/10.1039/c4sc00971a.

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15

Yang, Zhen, Kun Jiang, Ying-Chun Chen, and Ye Wei. "Copper-Catalyzed Dihydroquinolinone Synthesis from Isocyanides and O-Benzoyl Hydroxylamines." Journal of Organic Chemistry 84, no. 6 (2019): 3725–34. http://dx.doi.org/10.1021/acs.joc.9b00262.

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16

Endo, Yasuyuki, Ken-ichiro Kataoka, Naoki Haga, and Koichi Shudo. "Acid-catalyzed rearrangement of O-(2-arylphenyl)hydroxylamines to aryldihydroazepinones." Tetrahedron Letters 33, no. 23 (1992): 3339–42. http://dx.doi.org/10.1016/s0040-4039(00)92083-5.

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17

Matoušek, Václav, Ewa Pietrasiak, Lukas Sigrist, Barbara Czarniecki, and Antonio Togni. "O-Trifluoromethylation ofN,N-Disubstituted Hydroxylamines with Hypervalent Iodine Reagents." European Journal of Organic Chemistry 2014, no. 15 (2014): 3087–92. http://dx.doi.org/10.1002/ejoc.201402225.

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18

Egart, Boris, Dieter Lentz, and Constantin Czekelius. "ChemInform Abstract: Diastereoselective Bromocyclization of O-Allyl-N-tosyl-hydroxylamines." ChemInform 44, no. 30 (2013): no. http://dx.doi.org/10.1002/chin.201330143.

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19

Zhu, Haibo, Yajing Shen, Qinyue Deng, and Tao Tu. "Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature." Chemical Communications 51, no. 92 (2015): 16573–76. http://dx.doi.org/10.1039/c5cc06069a.

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20

Staszak, Michael A., and Christopher W. Doecke. "The use of N,O-bis(tert-butoxycarbonyl)-hydroxylamine in the synthesis of N-hydroxylamines and hydroxamic acids." Tetrahedron Letters 35, no. 33 (1994): 6021–24. http://dx.doi.org/10.1016/0040-4039(94)88064-6.

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21

Lv, Yunhe, Xin Wang, Hao Cui, et al. "Selectfluor-mediated highly selective radical dioxygenation of alkenes." RSC Advances 6, no. 78 (2016): 74917–20. http://dx.doi.org/10.1039/c6ra16266e.

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22

Dao, Rina, Xinyu Wang, Kexian Chen, Chenxuan Zhao, Jia Yao, and Haoran Li. "Landscape of the structure–O–H bond dissociation energy relationship of oximes and hydroxylamines." Physical Chemistry Chemical Physics 19, no. 33 (2017): 22309–20. http://dx.doi.org/10.1039/c7cp03809g.

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23

Zhao, He, Xiuwen Chen, Huanfeng Jiang та Min Zhang. "Copper-catalysed dehydrogenative α-C(sp3)–H amination of tetrahydroquinolines with O-benzoyl hydroxylamines". Organic Chemistry Frontiers 5, № 4 (2018): 539–43. http://dx.doi.org/10.1039/c7qo00794a.

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A copper-catalysed dehydrogenative α-C(sp<sup>3</sup>)–H amination of tetrahydroquinolines with O-benzoyl hydroxylamines has been demonstrated, which enables direct access to 2-alkylaminoquinolines in efficient manner.

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24

Hill, Jarvis, and David Crich. "Synthesis of O-tert-Butyl-N,N-disubstituted Hydroxylamines by N–O Bond Formation." Organic Letters 23, no. 16 (2021): 6396–400. http://dx.doi.org/10.1021/acs.orglett.1c02215.

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25

Wang, Yuzhuo, Lei Wang, Mingjie Chen, Youshao Tu, Yu Liu, and Junliang Zhang. "Palladium/Xu-Phos-catalyzed asymmetric carboamination towards isoxazolidines and pyrrolidines." Chemical Science 12, no. 23 (2021): 8241–45. http://dx.doi.org/10.1039/d1sc01337h.

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The new chiral ligand (S,Rs)-Xu4 with ortho-O<sup>i</sup>Pr showed good performance in the asymmetric carboamination reaction of N-Boc-O-homoallyl-hydroxylamines and N-Boc-pent-4-enylamines with aryl or alkenyl bromides.

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26

Lovato, Kaitlyn, Urmibhusan Bhakta, Yi Pin Ng, and László Kürti. "O-Cyclopropyl hydroxylamines: gram-scale synthesis and utility as precursors for N-heterocycles." Organic & Biomolecular Chemistry 18, no. 17 (2020): 3281–87. http://dx.doi.org/10.1039/d0ob00611d.

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A novel and scalable synthesis of O-cyclopropyl hydroxylamines is reported. These compounds are bench-stable and have been shown to be practical precursors for the synthesis of N-heterocycles via a di-heteroatom [3,3]-sigmatropic rearrangement.

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27

Zhou, Shuangliu, Zhiyong Yang, Xu Chen, et al. "Copper-Catalyzed Electrophilic Amination of Organoaluminum Nucleophiles with O-Benzoyl Hydroxylamines." Journal of Organic Chemistry 80, no. 12 (2015): 6323–28. http://dx.doi.org/10.1021/acs.joc.5b00767.

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28

Quiclet-Sire, Béatrice, Daniel Woollaston, and Samir Z. Zard. "A versatile radical based approach to O-alkylated hydroxylamines and oximes." Tetrahedron 64, no. 52 (2008): 11917–24. http://dx.doi.org/10.1016/j.tet.2008.08.113.

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29

Shen, Guodong, Lingyu zhao, Yichen Wang та Tongxin Zhang. "Room temperature copper-catalyzed oxidative amidation of terminal alkynes for the synthesis of α-ketoamides using O-benzoyl hydroxylamines as aminating reagent and oxidant". RSC Advances 6, № 82 (2016): 78307–10. http://dx.doi.org/10.1039/c6ra15219h.

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A novel and convenient copper-catalyzed oxidative amidation for the synthesis of α-ketoamides has been successfully developed, which uses easily available O-benzoyl hydroxylamines as aminating reagent and oxidant.

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30

Harger, Martin J. P., and P. Andrew Shimmin. "N-(dialkylphosphinoyl)hydroxylamines : Preparation using N,O-bis(trimethylsilyl)hydroxylamine and migration of simple alkyl groups in the rearrangements of their O-p-nitrobenzenesulphonates." Tetrahedron 48, no. 36 (1992): 7539–50. http://dx.doi.org/10.1016/s0040-4020(01)90367-9.

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31

HENMI, T., T. SAKAMOTO, and Y. KIKUGAWA. "ChemInform Abstract: Preparation of O-(2-(2-Pyridyl)ethyl)- and O-(2-(Trimethylsilyl)ethyl) hydroxylamines." ChemInform 25, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199425083.

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32

Bates, Roderick W., Jutatip Boonsombat, Yongna Lu, et al. "N,O-Heterocycles as synthetic intermediates." Pure and Applied Chemistry 80, no. 4 (2008): 681–85. http://dx.doi.org/10.1351/pac200880040681.

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Hydroxylamines can be cyclized under various conditions according to the nature of the unsaturation in the N-substituent. Both isoxazolidines and tetrahydrooxazines can be formed with good synthetic control. The choice of the appropriate cyclization reaction leads to syntheses of the natural products sedamine and monomorine. The related N,O-acetals are shown to undergo efficient ring-opening under Sakurai conditions.

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33

STASZAK, M. A., and C. W. DOECKE. "ChemInform Abstract: The Use of N,O-bis(tert-Butoxycarbonyl)-hydroxylamine in the Synthesis of N-Hydroxylamines and Hydroxamic Acids." ChemInform 26, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199501115.

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34

OHKATSU, Yasukazu, Kazuo YAMAGUCHI, and Yasushi KAWADA. "Reactivities of O-Alkyl Hydroxylamines Derived from Bis-(2,2,6,6-tetramethyl-piperidinyl)-sebacate." Journal of The Japan Petroleum Institute 37, no. 4 (1994): 400–404. http://dx.doi.org/10.1627/jpi1958.37.400.

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35

Boyles, David C., Timothy T. Curran, Derek Greene, Dainius Macikenas, and Roger V. Parlett. "Novel, base-promoted reaction of N-alkoxycarbonyl-O-(halosubstituted 4-nitrophenyl)hydroxylamines." Tetrahedron Letters 43, no. 38 (2002): 6735–37. http://dx.doi.org/10.1016/s0040-4039(02)01536-8.

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36

Khomutov, A. R., A. M. Kritsky, E. Yu Artamonova, and R. M. Khomutov. "Polyfunctional O-Substituted Hydroxylamines: Modification of Nucleic Acids, Inhibition of Sam-Decarboxylase." Nucleosides and Nucleotides 6, no. 1-2 (1987): 359–62. http://dx.doi.org/10.1080/07328318708056221.

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37

Nikitin, Kirill V., and Nonna P. Andryukhova. "Cleavage of the N–O bond in substituted hydroxylamines under basic conditions." Mendeleev Communications 10, no. 1 (2000): 32–33. http://dx.doi.org/10.1070/mc2000v010n01abeh001206.

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38

Kumar, Sonali, Rashi Sharma, Megan Garcia, et al. "Chemoselective Amide Formation Using O-(4-Nitrophenyl)hydroxylamines and Pyruvic Acid Derivatives." Journal of Organic Chemistry 77, no. 23 (2012): 10835–45. http://dx.doi.org/10.1021/jo302175g.

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39

ENDO, Y., K. KATAOKA, N. HAGA, and K. SHUDO. "ChemInform Abstract: Acid-Catalyzed Rearrangement of O-(2-Arylphenyl)hydroxylamines to Aryldihydroazepinones." ChemInform 23, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199248093.

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40

Rao, Wei-Hao, Qi Li, Li-Li Jiang, et al. "Copper-Catalyzed Intermolecular C(sp2)–H Amination with Electrophilic O-Benzoyl Hydroxylamines." Journal of Organic Chemistry 86, no. 15 (2021): 10580–90. http://dx.doi.org/10.1021/acs.joc.1c01229.

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41

Yoon, Hongju, Yuna Kim, and Yunmi Lee. "Cu-Catalyzed electrophilic amination of internal alkynes via hydroalumination." Organic & Biomolecular Chemistry 15, no. 4 (2017): 790–95. http://dx.doi.org/10.1039/c6ob02606k.

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A straightforward and efficient method for the synthesis of 1,2-diaryl-substituted enamines through the Cu-catalyzed electrophilic amination reaction of O-benzoyl hydroxylamines with vinylaluminum reagents generated in situ from the Ni-catalyzed hydroalumination of readily accessible internal aryl acetylenes is described.

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42

HARGER, M. J. P., and P. A. SHIMMIN. "ChemInform Abstract: N-(Dialkylphosphinoyl)hydroxylamines: Preparation Using N,O-Bis( trimethylsilyl)hydroxylamine and Migration of Simple Alkyl Groups in the Rearrangements of Their O-p-Nitrobenzenesulfonates." ChemInform 23, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199252239.

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43

Li, Gang, Chunqi Jia, Kai Sun, et al. "Copper(ii)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3207–10. http://dx.doi.org/10.1039/c5ob00135h.

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Copper acetate-catalyzed C–H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields.

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44

Santos, Pedro P. O., Cristina L. Trindade, Ana M. Lobo, and Sundaresan Prabhakar. "Selective O-acylation of aromatic hydroxylamines by 2-acylimidazolium and 2-acylbenzimidazolium salts." Tetrahedron Letters 34, no. 23 (1993): 3793–96. http://dx.doi.org/10.1016/s0040-4039(00)79231-8.

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45

Santos, Paulo F., Ana M. Lobo, and Sundaresan Prabhakar. "A Convenient Method for the Preparation ofN-Aryl andN-Alkyl-O-Methyl Hydroxylamines." Synthetic Communications 25, no. 22 (1995): 3509–18. http://dx.doi.org/10.1080/00397919508015485.

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46

Brömme, D., A. Schierhorn, H. Kirschke, et al. "Potent and selective inactivation of cysteine proteinases with N-peptidyl-O-acyl hydroxylamines." Biochemical Journal 263, no. 3 (1989): 861–66. http://dx.doi.org/10.1042/bj2630861.

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A series of N-peptidyl-O-acyl hydroxylamines was synthesized and tested as inactivators of cysteine proteinases. Depending on the structure of the peptidyl residue of the inhibitors, rapid and complete irreversible inactivation of the lysosomal cathepsins, B, L and S, may be achieved. The most effective inhibitors display second-order rate constants of the inactivation in the range 10(5)-10(6) M-1.s-1. By contrast, the activity of the aminoendopeptidase cathepsin H is only negligibly affected by the N-terminal-protected peptidyl inhibitors.

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47

Nagakubo, Hiroshi, Gou Kubota, Kanji Kubo, Tsuyoshi Kaneko, Tadamitsu Sakurai, and Hiroyasu Inoue. "Self-Sensitized Photolysis ofN-(1-Naphthoyl)-N-phenyl-O-(benzoyl-substituted benzoyl)hydroxylamines." Bulletin of the Chemical Society of Japan 69, no. 9 (1996): 2603–11. http://dx.doi.org/10.1246/bcsj.69.2603.

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48

Eve, Tom S. C., Andrew Wells, and Nicholas J. Turner. "Enantioselective oxidation of O-methyl-N-hydroxylamines using monoamine oxidase N as catalyst." Chemical Communications, no. 15 (2007): 1530. http://dx.doi.org/10.1039/b617537f.

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49

Zhou, Shuangliu, Zhiyong Yang, Xu Chen, et al. "ChemInform Abstract: Copper-Catalyzed Electrophilic Amination of Organoaluminum Nucleophiles with O-Benzoyl Hydroxylamines." ChemInform 46, no. 44 (2015): no. http://dx.doi.org/10.1002/chin.201544047.

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50

Matousek, Vaclav, Ewa Pietrasiak, Lukas Sigrist, Barbara Czarniecki, and Antonio Togni. "ChemInform Abstract: O-Trifluoromethylation of N,N-Disubstituted Hydroxylamines with Hypervalent Iodine Reagents." ChemInform 46, no. 6 (2015): no. http://dx.doi.org/10.1002/chin.201506074.

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