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Journal articles on the topic 'Pyridine-N-oxides'

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Published: 5 June 2025

Last updated: 24 June 2025

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1

Andreev, V. P. "Relative nucleophilic reactivity of pyridines and pyridine N-oxides (supernucleophilicity of pyridine N-oxides)." Russian Journal of Organic Chemistry 45, no. 7 (2009): 1061–69. http://dx.doi.org/10.1134/s1070428009070136.

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2

Abraham, Michael H., Lesya Honcharova, Silvana A. Rocco, William E. Acree, Jr, and Karina M. De Fina. "The lipophilicity and hydrogen bond strength of pyridine-N-oxides and protonated pyridine-N-oxides." New Journal of Chemistry 35, no. 4 (2011): 930. http://dx.doi.org/10.1039/c0nj00893a.

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3

Wrzeszcz, Zuzanna, and Renata Siedlecka. "Heteroaromatic N-Oxides Modified with a Chiral Oxazoline Moiety, Synthesis and Catalytic Applications." Catalysts 11, no. 4 (2021): 444. http://dx.doi.org/10.3390/catal11040444.

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Interesting properties of N-oxides and pyridine oxazoline compounds have become the starting point to synthesize compounds connecting both groups. A multi-step synthesis of a series of chiral oxazoline substituted pyridine N-oxides, alkyl derived of pyridine N-oxides, bipyridine N-oxides, and isoquinoline N-oxides, based on amino alcohols derived from natural amino acids or other previously prepared, is presented herein. Various synthetic pathways have been designed and tested according to the properties and limitations imposed by the target products. The encountered problems related to the stability of the products were discussed. The resulting compounds (eighteen structures) were tested as catalysts in th e allylation of benzaldehyde (obtaining up to 79% ee) as well as in nitroaldol reaction (obtaining up to 48% ee).

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4

Hisano, Takuzo, Kazunobu Harano, Toshikazu Matsuoka, Ryuichi Fukuoka, Motoji Murase, and Hirotoshi Yamada. "Pericyclic Reactions of Pyridine N-Oxides." HETEROCYCLES 23, no. 1 (1985): 173. http://dx.doi.org/10.3987/r-1985-01-0173.

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5

Chmurzynski, L., and Z. Warnke. "Acid-Base Equilibria of Substituted Pyridine N-Oxides in N,N-Dimethylformamide and Dimethyl Sulfoxide." Australian Journal of Chemistry 46, no. 2 (1993): 185. http://dx.doi.org/10.1071/ch9930185.

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Acidity constants have been determined potentiometrically for a variety of conjugate acids of substituted pyridine N-oxides in N,N- dimethylformamide ( dmf ) and dimethyl sulfoxide ( dmso ). The pKa values in these solvents varied in the same direction and correlated with the pKa values of these species in water and in the protophobic aprotic solvent acetonitrile. Further, a linear relationship has been established between the pKa values in the two protophilic aprotic solvents under study. The most basic substituted pyridine N-oxides exhibited a weak tendency towards cationic homoconjugation in dmf , whereas in the more basic dmso the homoconjugation equilibrium was not established for any of the heterocyclic N-oxides. The phenomenon of cationic homoconjugation was also not observed with pyridine as a representative of heterocyclic amines, both in dmf and dmso. This finding complies with the results obtained in other polar aprotic solvents.

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6

Greenberg, Arthur, Alexa R. Green, and Joel F. Liebman. "Computational Study of Selected Amine and Lactam N-Oxides Including Comparisons of N-O Bond Dissociation Enthalpies with Those of Pyridine N-Oxides." Molecules 25, no. 16 (2020): 3703. http://dx.doi.org/10.3390/molecules25163703.

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A computational study of the structures and energetics of amine N-oxides, including pyridine N-oxides, trimethylamine N-oxide, bridgehead bicyclic amine N-oxides, and lactam N-oxides, allowed comparisons with published experimental data. Most of the computations employed the B3LYP/6-31G* and M06/6-311G+(d,p) models and comparisons were also made between the results of the HF 6-31G*, B3LYP/6-31G**, B3PW91/6-31G*, B3PW91/6-31G**, and the B3PW91/6-311G+(d,p) models. The range of calculated N-O bond dissociation energies (BDE) (actually enthalpies) was about 40 kcal/mol. Of particular interest was the BDE difference between pyridine N-oxide (PNO) and trimethylamine N-oxide (TMAO). Published thermochemical and computational (HF 6-31G*) data suggest that the BDE of PNO was only about 2 kcal/mol greater than that of TMAO. The higher IR frequency for N-O stretch in PNO and its shorter N-O bond length suggest a greater difference in BDE values, predicted at 10–14 kcal/mol in the present work. Determination of the enthalpy of sublimation of TMAO, or at least the enthalpy of fusion and estimation of the enthalpy of vaporization might solve this dichotomy. The “extra” resonance stabilization in pyridine N-oxide relative to pyridine was consistent with the 10–14 kcal/mol increase in BDE, relative to TMAO, and was about half the “extra” stabilization in phenoxide, relative to phenol or benzene. Comparison of pyridine N-oxide with its acyclic model nitrone (“Dewar-Breslow model”) indicated aromaticity slightly less than that of pyridine.

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7

Möhrle, Hans, and Robert Nießen. "Umsetzung von N-Alkylpyridinium-Salzen mit Hydroxylamin / Reaction of N-Alkylpyridinium Salts with Hydroxylamine." Zeitschrift für Naturforschung B 55, no. 5 (2000): 434–42. http://dx.doi.org/10.1515/znb-2000-0514.

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1-Methylpyridinium salts showed no reaction with excessive hydroxylamine, but nicotinic acid derivatives in HMPT gave the corresponding N-oxides. 3-Acetyl-1-methylpyridinium iodide generated the hydroximino-pyridine 1-oxide 13 and the isoxazoles 14, 15E, and 15Z. 2- and 4-Cyano-l-methylpyridinium iodides underwent no ring cleavage, but altered only the functional group. However, the 3-cyano compound was converted into the corresponding pyridine N-oxides with carboxamide, hydroxyamidine and carbaldoxime groups.

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8

Igeta, Hiroshi, Yoshikuni Itoh, and Akio Ohsawa. "Flash Vacuum Pyrolysis of Pyridine N-Oxides." HETEROCYCLES 24, no. 1 (1986): 256. http://dx.doi.org/10.3987/r-1986-01-0256.

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9

Ohsawa, Akio, Takashi Itoh, Yoshikuni Itoh, and Hiroshi Igeta. "Flash Vaccum Pyrolysis of Pyridine N-Oxides." HETEROCYCLES 31, no. 5 (1990): 783. http://dx.doi.org/10.3987/com-90-5335.

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10

Belova, N. V., N. I. Giricheva, Yu A. Zhabanov, V. P. Andreev, and G. V. Girichev. "Sublimation Enthalpies of Substituted Pyridine N-Oxides." Russian Journal of General Chemistry 91, no. 10 (2021): 1932–37. http://dx.doi.org/10.1134/s1070363221100029.

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11

Bermejo, M. R., M. Teresa Lage, M. Isabel Fernández, and A. Castiñeiras. "Complexes of TlBr2l with Pyridine N-Oxide and Some Substituted Pyridine N-Oxides." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 17, no. 1 (1987): 79–92. http://dx.doi.org/10.1080/00945718708059415.

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12

Bermejo, M. R., A. García Deibe, A. Rodríguez, and A. Castiñeiras. "Complexes of Tlcl2I with Pyridine N-Oxide and some Substituted Pyridine N-Oxides." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 17, no. 7 (1987): 693–707. http://dx.doi.org/10.1080/00945718708059467.

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13

Rassadin, Valentin A., Dmitry P. Zimin, Gulnara Z. Raskil'dina, et al. "Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides." Green Chemistry 18, no. 24 (2016): 6630–36. http://dx.doi.org/10.1039/c6gc02556k.

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14

Puttreddy, Rakesh, Ondřej Jurček, Sandip Bhowmik, Toni Mäkelä, and Kari Rissanen. "Very strong −N–X+⋯−O–N+ halogen bonds." Chemical Communications 52, no. 11 (2016): 2338–41. http://dx.doi.org/10.1039/c5cc09487a.

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15

TSUKURIMICHI, Eiichi, Toshiaki YOSHIMURA, Hiroyuki NAKANISHI, and Yohichi SUGAWARA. "Pyrolysis of 2-(N-tosylalkanesulfinimidoyl)pyridine 1-oxides." NIPPON KAGAKU KAISHI, no. 7 (1985): 1424–28. http://dx.doi.org/10.1246/nikkashi.1985.1424.

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16

Ponomarenko, S. P., Yu Ya Borovikov, T. E. Sivachek, and V. P. Makovetskii. "Complex formation of pyridine N-oxides with iodine." Russian Journal of General Chemistry 74, no. 12 (2004): 1936–42. http://dx.doi.org/10.1007/s11176-005-0121-5.

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17

Londregan, Allyn T., Sandra Jennings, and Liuqing Wei. "Mild Addition of Nucleophiles to Pyridine-N-Oxides." Organic Letters 13, no. 7 (2011): 1840–43. http://dx.doi.org/10.1021/ol200352g.

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18

Cabral, Joana I. T. A., Ricardo A. R. Monteiro, Marisa A. A. Rocha, Luís M. N. B. F. Santos, William E. Acree, and Maria D. M. C. Ribeiro da Silva. "Molecular energetics of alkyl substituted pyridine N-oxides." Journal of Thermal Analysis and Calorimetry 100, no. 2 (2010): 431–39. http://dx.doi.org/10.1007/s10973-009-0646-7.

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19

Tang, Xiaodong, Nan Wu, Rongliang Zhai, et al. "Silver(i)-catalyzed addition of pyridine-N-oxides to alkynes: a practical approach for N-alkenoxypyridinium salts." Organic & Biomolecular Chemistry 17, no. 4 (2019): 966–72. http://dx.doi.org/10.1039/c8ob02907e.

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20

Kjellberg, Marianne, Alexia Ohleier, Pierre Thuéry, Emmanuel Nicolas, Lucile Anthore-Dalion, and Thibault Cantat. "Photocatalytic deoxygenation of N–O bonds with rhenium complexes: from the reduction of nitrous oxide to pyridine N-oxides." Chemical Science 12, no. 30 (2021): 10266–72. http://dx.doi.org/10.1039/d1sc01974k.

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21

Yamajala, Rajesh B. R. D. "Synthesis and characterization of penta-coordinated 2- and 4-substituted pyridine N-oxide silicon complexes." Mapana Journal of Sciences 19, no. 2 (2020): 11–19. http://dx.doi.org/10.12723/mjs.53.2.

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Novel penta-coordinated 2- and 4-substituted pyridine N-oxide silicon complexes were synthesized by the reaction of various 2- and 4-substituted pyridine N-oxides with silicon pinacolate. These complexes were characterized by 29Si NMR, 1H NMR and 13C NMR spectroscopy. The objectives of the present work is the study of influence of substitution at either 4 or 2-position of the pyridine N-oxide on the effect of the profile of pentacoordination.

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22

Drmanic, Sasa, Bratislav Jovanovic, Aleksandar Marinkovic, and Milica Misic-Vukovic. "Investigations of the reactivity of pyridine carboxylic acids with diazodiphenylmethane in protic and aprotic solvents: Part II: Pyridine mono-carboxylic acid N-oxides." Journal of the Serbian Chemical Society 71, no. 2 (2006): 89–101. http://dx.doi.org/10.2298/jsc0602089d.

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The rate constants for the reaction of three isomeric pyridine mono-carbocylic acid N-oxides with diazodiphenylmethane were determined at 30 ?C in thirty two protic and aprotic solvents by the well known UV spectrophotometric method. The rate constants are generally higher than for pyridine mono-carboxylic acids in a similar range of solvents, except for picolinic acid N-oxide, and also higher in protic than in aprotic solvents. The determined rate constants were correlated with solvent parameters using the Kamlet-Taft solvatochromic equation bymeans of multiple regression analysis. The sign of the equation coefficients were in agreement with the postulated reaction mechanism. The mode of the influences of the solvent is discussed on the basis of the correlation coefficients, taking into account the specific structures of the pyridine mono-carboxylic acid N-oxides.

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23

Denmark, Scott E., and Yu Fan. "Preparation of chiral bipyridine bis-N-oxides by oxidative dimerization of chiral pyridine N-oxides." Tetrahedron: Asymmetry 17, no. 4 (2006): 687–707. http://dx.doi.org/10.1016/j.tetasy.2005.12.039.

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24

Wang, Ruijia, Zebing Zeng, Chuang Chen, et al. "Fast regioselective sulfonylation of pyridine/quinoline N-oxides induced by iodine." Organic & Biomolecular Chemistry 14, no. 23 (2016): 5317–21. http://dx.doi.org/10.1039/c6ob00925e.

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25

Xu, Youguo, Sheng Zhang, Lijun Li, Yukang Wang, Zhenggen Zha, and Zhiyong Wang. "l-Phenylalanine potassium catalyzed asymmetric formal [3 + 3] annulation of 2-enoyl-pyridine N-oxides with acetone." Organic Chemistry Frontiers 5, no. 3 (2018): 376–79. http://dx.doi.org/10.1039/c7qo00796e.

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26

Wang, Dong, Zhenlin Liu, Zhentao Wang, Xinyue Ma, and Peng Yu. "Metal- and base-free regioselective thiolation of the methyl C(sp3)–H bond in 2-picoline N-oxides." Green Chemistry 21, no. 1 (2019): 157–63. http://dx.doi.org/10.1039/c8gc03072c.

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Metal- and base-free thiolation of the unactivated methyl C(sp<sup>3</sup>)–H bond in 2-picoline N-oxides with thiols is achieved by a one-pot, two-step sequence, including a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers.

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27

Hisano, Takuzo, Kazunobu Harano, Ikuo Shinohara, and Motoji Murase. "Pyridine N-Oxides as Catalysts for Thione-thiol Rearrangement." HETEROCYCLES 26, no. 10 (1987): 2583. http://dx.doi.org/10.3987/r-1987-10-2583.

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28

Liu, Chunli, Jiang Luo, Lingli Xu, and Zhibao Huo. "Synthesis of 2-substituted pyridines from pyridine N-oxides." Arkivoc 2013, no. 1 (2013): 154–74. http://dx.doi.org/10.3998/ark.5550190.0014.105.

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29

Mongin, Olivier, Patrick Rocca, Laurence Thomas-dit-Dumont, et al. "Metallation of pyridine N-oxides and application to synthesis." J. Chem. Soc., Perkin Trans. 1, no. 19 (1995): 2503–8. http://dx.doi.org/10.1039/p19950002503.

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30

Mai, Wenpeng, Jinwei Yuan, Zhicheng Li, et al. "Palladium-Catalyzed Benzylic Cross-Couplings of Pyridine N-Oxides." Synlett 23, no. 06 (2012): 938–42. http://dx.doi.org/10.1055/s-0031-1290602.

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31

Chelucci, Giorgio, Gabriele Murineddu, and Gerard A. Pinna. "Chiral pyridine N-oxides: useful ligands for asymmetric catalysis." Tetrahedron: Asymmetry 15, no. 9 (2004): 1373–89. http://dx.doi.org/10.1016/j.tetasy.2004.02.032.

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32

Zhang, Wen-Man, Jian-Jun Dai, Jun Xu, and Hua-Jian Xu. "Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides." Journal of Organic Chemistry 82, no. 4 (2017): 2059–66. http://dx.doi.org/10.1021/acs.joc.6b02891.

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33

Cho, S., W. Jo, J. Kim, and S. Choi. "C2-Alkylation of Pyridine N-Oxides with 1,1-Diborylalkanes." Synfacts 12, no. 11 (2016): 1222. http://dx.doi.org/10.1055/s-0036-1589406.

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34

KANIBOLOTSKII, A. L., V. A. MIKHAILOV, and V. A. SAVELOVA. "ChemInform Abstract: Reaction of Pyridine N-Oxides with Halogens." ChemInform 26, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199533159.

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35

Kanyiva, Kyalo Stephen, Yoshiaki Nakao, and Tamejiro Hiyama. "Nickel-Catalyzed Addition of Pyridine-N-oxides across Alkynes." Angewandte Chemie International Edition 46, no. 46 (2007): 8872–74. http://dx.doi.org/10.1002/anie.200703758.

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36

Kanyiva, Kyalo Stephen, Yoshiaki Nakao, and Tamejiro Hiyama. "Nickel-Catalyzed Addition of Pyridine-N-oxides across Alkynes." Angewandte Chemie 119, no. 46 (2007): 9028–30. http://dx.doi.org/10.1002/ange.200703758.

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37

Liu, Shanshan, Dieter Lentz, and C. Christoph Tzschucke. "ChemInform Abstract: Conversion of Pyridine N-Oxides to Tetrazolopyridines." ChemInform 45, no. 41 (2014): no. http://dx.doi.org/10.1002/chin.201441150.

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38

Pailloux, Sylvie L., Daniel Rosario-Amorin, Manab Chakravarty, et al. "Synthesis and Properties of New (Phosphinoylmethyl)Pyridine N-Oxides." Zeitschrift für anorganische und allgemeine Chemie 639, no. 7 (2013): 1101–16. http://dx.doi.org/10.1002/zaac.201300099.

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39

Belova, Natalya V., Nina I. Giricheva, and Mikhail S. Fedorov. "Substituent effect on the properties of pyridine-N-oxides." Structural Chemistry 26, no. 5-6 (2015): 1459–65. http://dx.doi.org/10.1007/s11224-015-0621-9.

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40

Zimmer, Reinhold, Hans-Ulrich Reissig, Lina Unger, Matteo Accorsi, Christian Eidamshaus, and Dorian Reich. "Preparation and Reactions of Trichloromethyl-Substituted Pyridine and Pyrimidine Derivatives." Synthesis 50, no. 20 (2018): 4071–80. http://dx.doi.org/10.1055/s-0037-1609576.

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The three-component reaction of lithiated methoxyallene, nitriles and trichloroacetic acid gave three model β-keto enamides that were starting materials for the synthesis of trichloromethyl-substituted pyridine and pyrimidine N-oxide derivatives. Upon treatment with acetic anhydride, the methyl group of the prepared pyrimidine N-oxides was converted into an acetoxymethyl group by a Boekelheide rearrangement. A few typical experiments also revealed that the trichloromethyl group of the prepared pyrimidine N-oxides can be replaced by an alkoxy or a hydroxy group, or transformed into an arylthiomethyl group. An alternative approach to β-keto enamides via the corresponding β-keto enamines was also examined and provided the expected 4-hydroxy-6-(trichloromethyl)pyridine derivative in good yield.

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41

Kim, Seung Woo, Tae-Woong Um та Seunghoon Shin. "Brønsted acid-catalyzed α-halogenation of ynamides from halogenated solvents and pyridine-N-oxides". Chemical Communications 53, № 18 (2017): 2733–36. http://dx.doi.org/10.1039/c6cc10286g.

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42

Jeong, Jinu, Kosuke Suzuki, Kazuya Yamaguchi, and Noritaka Mizuno. "Visible-light-responsive catalysis of a zinc-introduced lacunary disilicoicosatungstate for the deoxygenation of pyridine N-oxides." New Journal of Chemistry 41, no. 22 (2017): 13226–29. http://dx.doi.org/10.1039/c7nj03057f.

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43

Ide, Yuki, Nami Murai, Hiroki Ishimae, et al. "Spin-crossover between high-spin (S = 5/2) and low-spin (S = 1/2) states in six-coordinate iron(iii) porphyrin complexes having two pyridine-N oxide derivatives." Dalton Transactions 46, no. 1 (2017): 242–49. http://dx.doi.org/10.1039/c6dt03859j.

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44

Suresh, Rajendran, Rajendran Senthil Kumaran, Vajiram Senthilkumar та Shanmugam Muthusubramanian. "Silver catalyzed decarboxylative acylation of pyridine-N-oxides using α-oxocarboxylic acids". RSC Adv. 4, № 60 (2014): 31685–88. http://dx.doi.org/10.1039/c4ra05777e.

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45

Markham, Jonathan P., Ban Wang, Edwin D. Stevens, Stuart C. Burris, and Yongming Deng. "ortho ‐Alkylation of Pyridine N ‐Oxides with Alkynes by Photocatalysis: Pyridine N ‐Oxide as a Redox Auxiliary." Chemistry – A European Journal 25, no. 26 (2019): 6638–44. http://dx.doi.org/10.1002/chem.201901065.

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46

Murray, James I., Rudiger Woscholski, and Alan C. Spivey. "Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides – towards kinase-like reactivity." Chem. Commun. 50, no. 88 (2014): 13608–11. http://dx.doi.org/10.1039/c4cc05388e.

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47

Shen, Yan, Jiuxi Chen, Miaochang Liu, et al. "Copper-catalyzed direct C–H arylation of pyridine N-oxides with arylboronic esters: one-pot synthesis of 2-arylpyridines." Chem. Commun. 50, no. 33 (2014): 4292–95. http://dx.doi.org/10.1039/c3cc48767a.

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48

Uematsu, Tsubasa, Yoshiyuki Ogasawara, Kosuke Suzuki, Kazuya Yamaguchi, and Noritaka Mizuno. "Platinum-supporting hollandite-type vanadium–chromium mixed oxides as efficient heterogeneous catalysts for deoxygenation of sulfoxides under atmospheric H2 pressure." Catalysis Science & Technology 7, no. 9 (2017): 1912–20. http://dx.doi.org/10.1039/c7cy00547d.

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49

Toganoh, Motoki, Keitaro Fujino, Shinya Ikeda, and Hiroyuki Furuta. "Catalytic deoxygenation of pyridine N-oxides with N-fused porphyrin rhenium complexes." Tetrahedron Letters 49, no. 9 (2008): 1488–91. http://dx.doi.org/10.1016/j.tetlet.2007.12.117.

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50

Shibata, Takanori, and Hideaki Takano. "Cationic iridium-catalyzed C–H alkylation of 2-substituted pyridine N-oxides with acrylates." Organic Chemistry Frontiers 2, no. 4 (2015): 383–87. http://dx.doi.org/10.1039/c4qo00355a.

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