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Journal articles on the topic 'N-substituted hydroxylamines'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

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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2

Svoboda, Jiří, and Jaroslav Paleček. "Synthesis of N-[(3-substituted phenoxy)alkyl]acetohydroxamic acids, potential inhibitors of the enzyme 5-lipoxygenase." Collection of Czechoslovak Chemical Communications 56, no. 6 (1991): 1317–32. http://dx.doi.org/10.1135/cccc19911317.

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The synthesis of the title compounds starts from methyl (3-subst. phenoxy)alkanoates II which are reduced to the corresponding aldehydes and then transformed to oximes V by reaction with hydroxylamine. Reduction with borane-pyridine complex gives the hydroxylamines VI which on diacetylation and partial deacetylation provide the hydroxamic acids VIII.

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3

Beirakhov, A. G., I. M. Orlova, E. G. Il’in, et al. "Molybdenum(VI) complexes with N-substituted hydroxylamines." Russian Journal of Inorganic Chemistry 58, no. 12 (2013): 1446–51. http://dx.doi.org/10.1134/s003602361312005x.

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4

Li, Xiaoqing, Xiangsheng Xu, Kun Chen, et al. "Substrate-Controlled Regioselective Iodooxygenation of Olefins." Synlett 29, no. 12 (2018): 1634–38. http://dx.doi.org/10.1055/s-0037-1609968.

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An unexpected regioselective I2/TBHP-mediated 1,2-iodooxygenation of alkenes with N-hydroxylamines is described. The reaction proceeds through a radical coupling mechanism or a iodonium mechanism, which is controlled by the structures of both N-hydroxylamines and alkenes, to form vicinal iodo-substituted N-alkoxyamines regioselectively. Both the iodo and alkoxyamine group of the resulting products offer rich possibilities of synthetic manipulations.

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5

Varma, Rajender S., and George W. Kabalka. "A CONVENIENT ONE-POT PREPARATION OF N-SUBSTITUTED HYDROXYLAMINES." Organic Preparations and Procedures International 17, no. 4-5 (1985): 254–56. http://dx.doi.org/10.1080/00304948509355515.

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6

Guan, Zhaobing, Manman Ding, Yao Sun, et al. "The synthesis of two long-chain N-hydroxy amino coumarin compounds and their applications in the analysis of aldehydes." RSC Advances 7, no. 32 (2017): 19707–16. http://dx.doi.org/10.1039/c7ra02177a.

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7

Guthrie, Daryl A., Nam Y. Kim, Maxime A. Siegler, Cathy D. Moore, and John P. Toscano. "Development of N-Substituted Hydroxylamines as Efficient Nitroxyl (HNO) Donors." Journal of the American Chemical Society 134, no. 4 (2012): 1962–65. http://dx.doi.org/10.1021/ja2103923.

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8

Bezhan, I. P., K. N. Zelenin, L. A. Sviridova, et al. "Synthesis of isoxazolidine derivatives from N-substituted hydroxylamines and ?,?-unsaturated ketones." Chemistry of Heterocyclic Compounds 25, no. 6 (1989): 684–87. http://dx.doi.org/10.1007/bf00470030.

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9

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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10

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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11

Dulla, Balakrishna, Neelima D. Tangellamudi, Sridhar Balasubramanian, et al. "Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles." Organic & Biomolecular Chemistry 12, no. 16 (2014): 2552. http://dx.doi.org/10.1039/c3ob42460j.

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12

Nikitin, Kirill V., and Nonna P. Andryukhova. "ChemInform Abstract: Cleavage of the N-O Bond in Substituted Hydroxylamines under Basic Conditions." ChemInform 31, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200024048.

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13

Read de Alaniz, Javier, Leoni Palmer, and Charles Frazier. "Developments in Nitrosocarbonyl Chemistry: Mild Oxidation of N-Substituted Hydroxylamines Leads to New Discoveries." Synthesis 46, no. 03 (2013): 269–80. http://dx.doi.org/10.1055/s-0033-1338569.

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14

Frazier, Charles P., Alejandro Bugarin, Jarred R. Engelking, and Javier Read de Alaniz. "Copper-Catalyzed Aerobic Oxidation of N-Substituted Hydroxylamines: Efficient and Practical Access to Nitroso Compounds." Organic Letters 14, no. 14 (2012): 3620–23. http://dx.doi.org/10.1021/ol301414k.

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15

Yin, Zhiwei, Jinzhu Zhang, Jing Wu, et al. "Double Hetero-Michael Addition of N-Substituted Hydroxylamines to Quinone Monoketals: Synthesis of Bridged Isoxazolidines." Organic Letters 15, no. 14 (2013): 3534–37. http://dx.doi.org/10.1021/ol401235z.

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16

Katritzky, Alan R., Konstantina Yannakopoulou, Ping Lue, Danuta Rasala, and Laszlo Urogdi. "The chemistry of N-substituted benzotriazoles. Part 14. Novel routes to secondary and tertiary amines and to N, N-disubstituted hydroxylamines." Journal of the Chemical Society, Perkin Transactions 1, no. 2 (1989): 225. http://dx.doi.org/10.1039/p19890000225.

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17

Andoh, Fumihiko, Kanji Kubo, and Tadamitsu Sakurai. "Imine-Forming Radical Elimination Reactions ofO-(1-Naphthoyl)-N,N-bis(p-substituted benzyl)hydroxylamines Activated by Triplet Benzophenone." Bulletin of the Chemical Society of Japan 72, no. 11 (1999): 2537–42. http://dx.doi.org/10.1246/bcsj.72.2537.

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18

Hoffman, Robert V., and Jean M. Shankweiler. "Structural effects on the transition states of imine-forming eliminations in N-substituted O-(arylsulfonyl)hydroxylamines." Journal of the American Chemical Society 110, no. 12 (1988): 4019–22. http://dx.doi.org/10.1021/ja00220a048.

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19

Frazier, Charles P., Leoni I. Palmer, Andrey V. Samoshin, and Javier Read de Alaniz. "Accessing nitrosocarbonyl compounds with temporal and spatial control via the photoredox oxidation of N-substituted hydroxylamines." Tetrahedron Letters 56, no. 23 (2015): 3353–57. http://dx.doi.org/10.1016/j.tetlet.2015.01.024.

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20

Mahy, J. P., and D. Mansuy. "Formation of prostaglandin synthase-iron-nitrosoalkane inhibitory complexes upon in situ oxidation of N-substituted hydroxylamines." Biochemistry 30, no. 17 (1991): 4165–72. http://dx.doi.org/10.1021/bi00231a009.

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21

Palmer, Leoni I., Charles P. Frazier, and Javier Read de Alaniz. "ChemInform Abstract: Developments in Nitrosocarbonyl Chemistry: Mild Oxidation of N-Substituted Hydroxylamines Lead to New Discoveries." ChemInform 45, no. 17 (2014): no. http://dx.doi.org/10.1002/chin.201417269.

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22

Nelyubin, A. V., N. A. Selivanov, A. Yu Bykov, et al. "N-Borylated Hydroxylamines [B12H11NH2OH]– as a Novel Type of Substituted Derivative of the closo-Dodecaborate Anion." Russian Journal of Inorganic Chemistry 65, no. 6 (2020): 795–99. http://dx.doi.org/10.1134/s0036023620060133.

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23

Khuthier, Abdul Hussain, Khawla Y. Al-Mallah, Salim Y. Hanna, and Noor Aldeen I. Abdulla. "Studies of tertiary amine oxides. 9. Thermal rearrangement of 1-(4-substituted) phenylpiperidine N-oxides to the corresponding N-hydroxylamines." Journal of Organic Chemistry 52, no. 9 (1987): 1710–13. http://dx.doi.org/10.1021/jo00385a012.

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24

Mourad, M. Soubei, Rajender S. Varma, and George W. Kabalka. "Reduction of .alpha.,.beta.-unsaturated nitro compounds with boron hydrides: a new route to N-substituted hydroxylamines." Journal of Organic Chemistry 50, no. 1 (1985): 133–35. http://dx.doi.org/10.1021/jo00201a030.

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25

Frazier, Charles P., Alejandro Bugarin, Jarred R. Engelking, and Javier Read de Alaniz. "ChemInform Abstract: Copper-Catalyzed Aerobic Oxidation of N-Substituted Hydroxylamines: Efficient and Practical Access to Nitroso Compounds." ChemInform 43, no. 47 (2012): no. http://dx.doi.org/10.1002/chin.201247169.

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26

Patel, Pitambar, and Sukbok Chang. "N-Substituted Hydroxylamines as Synthetically Versatile Amino Sources in the Iridium-Catalyzed Mild C–H Amidation Reaction." Organic Letters 16, no. 12 (2014): 3328–31. http://dx.doi.org/10.1021/ol501338h.

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27

Yin, Zhiwei, Jinzhu Zhang, Jing Wu, et al. "ChemInform Abstract: Double Hetero-Michael Addition of N-Substituted Hydroxylamines to Quinone Monoketals: Synthesis of Bridged Isoxazolidines." ChemInform 44, no. 50 (2013): no. http://dx.doi.org/10.1002/chin.201350064.

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28

Ali, Sk Asrof, Azfar Hassan, and Mohammed I. M. Wazeer. "Nitrogen inversion and N–O bond rotation processes in di-and tri-substituted hydroxylamines. A dynamic NMR study." J. Chem. Soc., Perkin Trans. 2, no. 7 (1996): 1479–83. http://dx.doi.org/10.1039/p29960001479.

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29

Frazier, Charles P., Leoni I. Palmer, Andrey V. Samoshin, and Javier Read de Alaniz. "ChemInform Abstract: Accessing Nitrosocarbonyl Compounds with Temporal and Spatial Control via the Photoredox Oxidation of N-Substituted Hydroxylamines." ChemInform 46, no. 40 (2015): no. http://dx.doi.org/10.1002/chin.201540041.

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30

Patel, Pitambar, and Sukbok Chang. "ChemInform Abstract: N-Substituted Hydroxylamines as Synthetically Versatile Amino Sources in the Iridium-Catalyzed Mild C-H Amidation Reaction." ChemInform 45, no. 51 (2014): no. http://dx.doi.org/10.1002/chin.201451157.

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31

Fishbein, James C., and Robert A. McClelland. "Cyclohexadienes from the rearrangement of O-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines. Reaction in aqueous solution to meta- and para-substituted 2,6-dimethylacetanilides." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1995): 653. http://dx.doi.org/10.1039/p29950000653.

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32

GOTI, A., S. CICCHI, V. FEDI, L. NANNELLI, and A. BRANDI. "ChemInform Abstract: Synthesis of Enantiopure 3-Substituted Pyrroline N-Oxides by Highly Regioselective Oxidation of the Parent Hydroxylamines: A Mechanistic Rationale." ChemInform 28, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199737144.

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33

Lee, Katarzyna N., Dominique N. Spiegowski, Johnny W. Lee, Sanghyun Lim, Fuhua Zhao, and Ming-Yu Ngai. "Transition-metal-free C–H amidation and chlorination: synthesis of N/N′-mono-substituted imidazopyridin-2-ones from N-pyridyl-N-hydroxylamine intermediates." Chemical Communications 54, no. 50 (2018): 6935–38. http://dx.doi.org/10.1039/c8cc02425a.

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34

Möhrle, H., and R. Nießen. "Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 1. Mitteilung. N-(Nitrophenyl)-substituierte Verbindungen/Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 1st Communication. N-(Nitrophenyl) Substituted Compounds." Zeitschrift für Naturforschung B 54, no. 2 (1999): 225–33. http://dx.doi.org/10.1515/znb-1999-0211.

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N-(Nitrophenyl) substituted isoquinolinium salts reacted with nucleophiles of the hydroxylamine type to different products depending on the electron withdrawing strength of the substituent. Mononitro compound 8 produced only the cyclic hydroxylamine 9a, the trinitroderivative 5 solely the ring cleaved oximes. The dinitro substance 1 held an intermediate position and gave rise to a labile cyclic hydroxylamine and a more stable ring opened Z-enamine; hydroxylamine ethers generated cyclic products which showed in dimethylsulfoxide ring chain isomerism with the tautomers.

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35

Sabir, Shekh, Ganesh Kumar, and Jawahar L. Jat. "O-Substituted hydroxyl amine reagents: an overview of recent synthetic advances." Organic & Biomolecular Chemistry 16, no. 18 (2018): 3314–27. http://dx.doi.org/10.1039/c8ob00146d.

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Reagents derived from oxygen-substituted hydroxylamine facilitate stereo- and regioselective C–N, N–N, O–N, and S–N bond-formation reactions and intra-molecular cyclizations without any expensive metal catalysts. These remarkable transformations are discussed in this review.

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36

Bakthadoss, Manickam, and Mohammad Mushaf. "Intramolecular [3 + 2] nitrone cycloaddition reaction: highly regio and diastereoselective synthesis of bicyclo[3.2.1]octane scaffolds." Organic & Biomolecular Chemistry 18, no. 47 (2020): 9653–59. http://dx.doi.org/10.1039/d0ob01960g.

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Development of a regio- and a diastereoselective protocol for the synthesis of bicyclo[3.2.1]octane frameworks from vinylogous carbonates and N-substituted hydroxylamine hydrochlorides via intramolecular 1,3-dipolar nitrone cycloaddition reaction.

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37

Sun, Bin, Shi Yin, Xiaohui Zhuang, Can Jin, and Weike Su. "Selectfluor-induced C(sp2)–O coupling reaction of N-substituted anilines with hydroxylamine derivatives." Organic & Biomolecular Chemistry 16, no. 33 (2018): 6017–24. http://dx.doi.org/10.1039/c8ob01348a.

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We developed a novel metal-free method for the construction of C(sp<sup>2</sup>)–O bonds via oxidative cross-coupling reactions between various N-substituted anilines and hydroxylamine derivatives just using commercially available Selectfluor as an oxidant.

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38

Comanita, Eugenia, Gheorghe Roman, Irina Popovici, and Bogdan Comanita. "Synthesis and reactivity of some mannich bases. VIII. Studies on several mannich bases derived from ortho-hidroxyacetophenones and their conversion into oximino derivatives." Journal of the Serbian Chemical Society 66, no. 1 (2001): 9–16. http://dx.doi.org/10.2298/jsc0101009c.

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The synthesis of several Mannich bases resulting from the reaction of 2-hydroxy-4-methylacetophenone with paraformaldehyde and secondary amines is reported. Another series of products was obtained from N,N-dimethyl substituted Mannich bases by replacing the amino group with pyrrolidine. Most of the Mannich bases were transformed into oximes by treatment with hydroxylamine hydrochloride in 10% NaOH.

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39

Zimmer, Reinhold, Hans-Ulrich Reissig, Luise Schefzig, et al. "Access to Highly Substituted Pyrimidine N-Oxides and 4-Acetoxymethyl-Substituted Pyrimidines via the LANCA Three-Component Reaction–Cyclocondensation Sequence." Synthesis 53, no. 12 (2021): 2067–80. http://dx.doi.org/10.1055/s-0040-1706020.

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AbstractThe LANCA three-component reaction of lithiated alkoxyallenes (LA), nitriles (N), and carboxylic acids (CA) smoothly provides β-alkoxy-β-ketoenamides in broad structural variety. The subsequent cyclocondensation of these compounds with hydroxylamine hydrochloride afforded a large library of pyrimidine N-oxides under mild conditions and in good yields. Their synthetic utility was further increased by the Boekelheide rearrangement leading to 4-acetoxymethyl-substituted pyrimidines. With trifluoroacetic anhydride the rearrangement proceeds even at room temperature and directly furnishes

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40

Souldozi, Ali, Jabbar Khalafy, Ahmad Poursattar Marjani, Katarzyna Ślepokura, Tadeusz Lis, and Ali Ramazani. "Synthesis and Single Crystal X-Ray Structure of Ethyl 2-(1,3-Benzoxazol- 2-yl)-5-oxo-3-(4-toluidino)-2,5-dihydro-4-isoxazolecarboxylate." Zeitschrift für Naturforschung B 62, no. 5 (2007): 705–10. http://dx.doi.org/10.1515/znb-2007-0513.

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Abstract Ethyl 5-oxo-3-(4-toluidino)-2,5-dihydro-4-isoxazolecarboxylate was prepared from the reaction of diethyl 2-(4-toluidinocarbothioyl)malonate with hydroxylamine. Its reaction with 2- chlorobenzoxazole gave the corresponding N-substituted isoxazolone. The structure of the final product 4 was confirmed by IR, 1H and 13C NMR spectroscopy and mass spectrometry, and by X-ray single crystal structure determination.

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41

Möhrle, H., and R. Nießen. "Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 3. Mitteilung. Mechanismus der Aminoxid-Bildung / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 3rd Communication. Mechanism of Amine Oxide Generation." Zeitschrift für Naturforschung B 54, no. 7 (1999): 913–22. http://dx.doi.org/10.1515/znb-1999-0715.

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2-Methylpapaverinium iodide (1) reacted with hydroxylamine to papaverine-N-oxide (2), but without a detectable intermediate and only in moderate yield, caused by the steric hindrance of the 1-substituent. The ring opened product of 2-dinitrophenylisoquinolinium salt with hydroxylamine, the enamine-oxime 3b gave rise to a 3-substituted cyclic nitrone (6), when heated with triethylamine. This alkali-stable compound was transformed with acid quantitatively to isoquinoline-N-oxide (4). The enaminonitrile 9c, treated with triethylamine showed cyclization to the iminoisoquinoline 10, which by loss o

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42

Möhrle, H., and R. Nießen. "Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 2. Mitteilung N-(Alkyl)- und N-(Aryl)-substituierte Verbindungen / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 2nd Communication N-(Alkyl) and N-(Aryl) Substituted Compounds." Zeitschrift für Naturforschung B 54, no. 4 (1999): 532–40. http://dx.doi.org/10.1515/znb-1999-0417.

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The N -alkyl- and N -aryl-isoquinolinium salts 7, 15-17 reacted with free hydroxylamine in pyridine to give the isoquinoline-2-oxide (9) as final product. The intermediate dioximes 8 were isolated and characterized by derivatisation with acetic anhydride to the oxime ester nitrile 10. From the reaction o f 8 with trifluoroacetic anhydride/triethylam ine 3-amino-isoquinoline- 2-oxide (12) resulted after hydrolysis. Due to the electronic influence the 5-nitroisoquinolinium salts 1 -3 react faster than the 5-hydroxy derivative 20. but with the same course of conversion via dioximes to amine oxide

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43

Cherton, Jean-Claude, Marc Lanson, Daïf Ladjama, Yvette Guichon та Jean-Jacques Basselier. "Synthèse d'isoxazoles substitués en α de l'azote par une chaine alkyle ou alcényle". Canadian Journal of Chemistry 68, № 8 (1990): 1271–76. http://dx.doi.org/10.1139/v90-196.

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Several syntheses of special isoxazoles bearing a long alkyl or alkenyl side chain in the α position of the nitrogen are presented. A very convenient route in the case of an alkyl side chain is the classical 1,3-dipolar cycloaddition of a nitrile-oxide to a vinyl acetate. Although it is a rather long approach, the reaction of hydroxylamine with enone-epoxides represents a new and unequivocal method compatible with alkenyl side chains. The isomerisation of the easily synthesized isoxazoles bearing such substitutents α to the oxygen, by the reaction of their isoxazolium salts with hydroxylamine,

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44

Et al., Haddad. "Synthesis and Characterization of New Selenonitrone Derivative and Its Effect on Breast Cancer Cell Line Viability in Vitro." Baghdad Science Journal 16, no. 3(Suppl.) (2019): 0754. http://dx.doi.org/10.21123/bsj.2019.16.3(suppl.).0754.

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New nitrone and selenonitrone compounds were synthesized. The condensation method between N-(2-hydroxyethyl) hydroxylamine and substituted carbonyl compounds such as [benzil, 4, 4́-dichlorobenzil and 2,2́ -dinitrobenzil] afforded a variety of new nitrone compounds while the condensation between N-benzylhydroxylamine and substituted selenocarbonyl compounds such as [di(4-fluorobenzoyl) diselenide and (4-chlorobenzoyl selenonitrile] obtained selenonitrone compounds. The condensation of N-4-chlorophenylhydroxylamine with dibenzoyl diselenide obtained another type of selenonitrone compounds. The s

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45

Stewart, Andrew O., and Dee W. Brooks. "N,O-Bis(phenoxycarbonyl)hydroxylamine: a new reagent for the direct synthesis of substituted N-hydroxyureas." Journal of Organic Chemistry 57, no. 18 (1992): 5020–23. http://dx.doi.org/10.1021/jo00044a046.

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46

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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47

Kabirifard, Hassan, Pardis Hafez Taghva, Hossein Teimouri, et al. "Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles." Heteroatom Chemistry 2020 (July 8, 2020): 1–9. http://dx.doi.org/10.1155/2020/5945796.

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The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioes

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48

STEWART, A. O., and D. W. BROOKS. "ChemInform Abstract: N,O-Bis(phenoxycarbonyl)hydroxylamine: A New Reagent for the Direct Synthesis of Substituted N-hydroxyureas." ChemInform 24, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199305154.

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49

Kliegel, Wolfgang, Jörg Metge, Steven J. Rettig, and James Trotter. "C-(2-Hydroxyaryl)-N-(2-hydroxyphenylmethyl)nitrones as regioselective bidentate ligands in boron chelate formation. Crystal and molecular structures of a diphenylboron complex and its parent ligand." Canadian Journal of Chemistry 76, no. 7 (1998): 1082–92. http://dx.doi.org/10.1139/v98-096.

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Abstract:

The C-(2-hydroxyaryl)-N-(2-hydroxyphenylmethyl)nitrones 5 are synthesized by the condensation of variously substituted salicylaldehydes with N-(2-hydroxyphenylmethyl)-hydroxylamine. These nitrones react with diphenylborinic acid anhydride to form seven-membered diphenylboron chelates 6. Crystals of C-(4-diethylamino-2-hydroxyphenyl)-N-(2-hydroxyphenylmethyl)nitrone, 5d, are monoclinic, a = 6.911(2), b = 10.663(2), c = 22.951(1) Å, β = 97.33(1)°, Z = 4, space group P21/n, and those of 4-dimethylamino-8-(2-hydroxyphenylmethyl)-6,6-diphenyl-5,7-dioxa-8-azonia-6-borata-6,7-dihydro-5H-benzocyclohep

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Bencková, Mária, and Alžbeta Krutošíková. "5-Aminofuro[3,2-c]pyridinium Tosylates and Substituted Furo[3,2-c]pyridine N-Oxides: Synthesis and Reactions." Collection of Czechoslovak Chemical Communications 64, no. 3 (1999): 539–47. http://dx.doi.org/10.1135/cccc19990539.

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Abstract:

5-Aminofuro[3,2-c]pyridinium tosylates 2a-2c were synthesized by direct N-amination of furo[3,2-c]pyridines 1a-1c with O-(4-methylbenzenesulfonyl)hydroxylamine in dichloromethane. Zwitterionic furo[3,2-c]pyridinium N-imides 3a-3c generated from 2a-2c and anhydrous potassium carbonate in N,N-dimethylformamide afforded by 1,3-dipolar cycloaddition reactions with dimethyl butynedioate or ethyl propiolate the corresponding furo[3,2-c]pyrazolo[1,5-a]pyridinecarboxylic esters 4a-4c and 5a-5c. Furo[3,2-c]pyridine N-oxides 6a-6c and their benzo derivative 6d were synthesized by reaction of 1 with 3-ch

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