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Journal articles on the topic 'Heteroaromatic N-Oxides'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Xu, P., and H. C. Xu. "Electrochemical Deoxygenation of N-Heteroaromatic N-Oxides." Synlett 30, no. 10 (2019): 1219–21. http://dx.doi.org/10.1055/s-0037-1611541.

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An electrochemical method for the deoxygenation of N-heteroaromatic N-oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

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2

NEETA, SINHA, and SINHA R. "Rearrangement of Heteroaromatic N-Oxides. Synthesis of Chloromethylquinoline A New." Journal of Indian Chemical Society Vol.71, Dec 1994 (1994): 763–64. https://doi.org/10.5281/zenodo.5895617.

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Chemistry Department, T. N. B. Postgraduate College, Bhagalpur University, Bhagalpur-812 007 <em>Manuscript received 29 September 1992, revised 3 August 1993, accepted 17 September 1993</em> Rearrangement of Heteroaromatic <em>N</em>-Oxides. Synthesis of Chloromethylquinoline A New

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3

Lantaño, Beatriz, Sebastián Barata-Vallejo, and Al Postigo. "Organic dye-photocatalyzed fluoroalkylation of heteroarene-N-oxide derivatives." Organic & Biomolecular Chemistry 16, no. 36 (2018): 6718–27. http://dx.doi.org/10.1039/c8ob01653d.

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A direct C<sub>Het</sub>–H perfluoroalkylation reaction of heteroaromatic-N-oxides has been achieved. Acid-catalyzed transformation of the perfluoroalkylated-N-oxides leads to 2-(perfluoroalkyl)benzo[f][1,3]oxazepines. De-oxygenation of the perfluoroalkylated heteroaromatic-N-oxides affords a regioselective radical perfluoroalkylation protocol.

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4

Jovanovic, Misa V. "π-Deficiency parameters of heteroaromatic N-oxides". Spectrochimica Acta Part A: Molecular Spectroscopy 41, № 10 (1985): 1135–39. http://dx.doi.org/10.1016/0584-8539(85)80123-9.

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5

Mohammad, Mehdi Khodaei, Alizadeh Abdolhamid, and Afshar Hezarkhani Hadis. "A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate." Journal of the Iranian Chemical Society 15 (May 2, 2018): 1843–49. https://doi.org/10.1007/s13738-018-1381-4.

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A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.

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6

Wrzeszcz, Zuzanna, and Renata Siedlecka. "Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review." Molecules 25, no. 2 (2020): 330. http://dx.doi.org/10.3390/molecules25020330.

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An increasing interest in the synthesis and use of optically active pyridine N-oxides as chiral controllers for asymmetric reactions has been observed in the last few years. Chiral heteroaromatic N-oxides can work as powerful electron-pair donors, providing suitable electronic environments in the transition state formed within the reaction. The nucleophilicity of the oxygen atom in N-oxides, coupled with a high affinity of silicon to oxygen, represent ideal properties for the development of synthetic methodology based on nucleophilic activation of organosilicon reagents. The application of chi

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7

Nizhnik, Yakov P., Erin Hansen, Cayden Howard, Matthias Zeller, and Sergiy V. Rosokha. "Complexes of Zinc-Coordinated Heteroaromatic N-Oxides with Pyrene: Lewis Acid Effects on the Multicenter Donor–Acceptor Bonding." Molecules 29, no. 14 (2024): 3305. http://dx.doi.org/10.3390/molecules29143305.

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4-Nitroquinoline-N-oxide (NQO) and 4-nitropyridine-N-oxide (NPO) are important precursors for the synthesis of substituted heterocycles while NQO is a popular model mutagen and carcinogen broadly used in cancer research; intermolecular interactions are critical for their reactions or functioning in vivo. Herein, the effects of the coordination of N-oxide’s oxygen atom to Lewis acids on multicenter donor–acceptor bonding were explored via a combination of experimental and computational studies of the complexes of NQO and NPO with a typical π-electron donor, pyrene. Coordination with ZnCl2 incre

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8

Hwang, Chiwon, Woohyun Jo, and Seung Hwan Cho. "Base-promoted, deborylative secondary alkylation of N-heteroaromatic N-oxides with internal gem-bis[(pinacolato)boryl]alkanes: a facile derivatization of 2,2′-bipyridyl analogues." Chemical Communications 53, no. 54 (2017): 7573–76. http://dx.doi.org/10.1039/c7cc03731g.

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A base-promoted, secondary alkylation of N-heteroaromatic N-oxides using internal gem-bis[(pinacolato)boryl]alkanes as alkylation reagents is achieved to form deoxygenated secondary alkylated N-heteroarenes.

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9

Lai, Miao, Ke Zhai, Chuance Cheng, Zhiyong Wu, and Mingqin Zhao. "Direct thiolation of aza-heteroaromatic N-oxides with disulfides via copper-catalyzed regioselective C–H bond activation." Organic Chemistry Frontiers 5, no. 20 (2018): 2986–91. http://dx.doi.org/10.1039/c8qo00840j.

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10

Sun, Kai, Xiao-Lan Chen, Xu Li, et al. "H-phosphonate-mediated sulfonylation of heteroaromatic N-oxides: a mild and metal-free one-pot synthesis of 2-sulfonyl quinolines/pyridines." Chemical Communications 51, no. 60 (2015): 12111–14. http://dx.doi.org/10.1039/c5cc04484g.

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11

Zhang, Liming, and Youliang Wang. "Recent Developments in the Chemistry of Heteroaromatic N-Oxides." Synthesis 47, no. 03 (2015): 289–305. http://dx.doi.org/10.1055/s-0034-1379884.

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12

Araki, Yuta, Koji Kobayashi, Misato Yonemoto, and Yoshinori Kondo. "Functionalisation of heteroaromatic N-oxides using organic superbase catalyst." Org. Biomol. Chem. 9, no. 1 (2011): 78–80. http://dx.doi.org/10.1039/c0ob00740d.

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13

Andreev, V. P., V. A. Tafeenko, and S. N. Ivashevskaya. "Molecular complexes of heteroaromatic N-oxides with boron trifluoride." Russian Journal of General Chemistry 84, no. 2 (2014): 255–58. http://dx.doi.org/10.1134/s1070363214020157.

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14

Ryzhakov, A. V. "Molecular complexes of heteroaromatic N-oxides with 2,4-dinitrophenylhydrazine." Russian Journal of General Chemistry 84, no. 8 (2014): 1644–45. http://dx.doi.org/10.1134/s1070363214080362.

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15

Wang, Hui, Yu Pei, Jie Bai, Jinli Zhang, Yangjie Wu, and Xiuling Cui. "Dimerization of heteroaromatic N-oxides under metal-free conditions." RSC Adv. 4, no. 50 (2014): 26244–46. http://dx.doi.org/10.1039/c4ra02820a.

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16

Andreev, V. P., A. V. Ryzhakov, A. K. Morozov, O. O. Alekseeva, and L. L. Rodina. "Donor-acceptor complexes of heteroaromatic N-oxides. A review." Chemistry of Heterocyclic Compounds 31, no. 6 (1995): 671–81. http://dx.doi.org/10.1007/bf01169067.

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17

ANDREEV, V. P., A. V. RYZHAKOV, A. K. MOROZOV, O. O. ALEKSEEVA, and L. L. RODINA. "ChemInform Abstract: Donor-Acceptor Complexes of Heteroaromatic N-Oxides." ChemInform 27, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199615321.

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18

Crisenza, Giacomo E. M., Elizabeth M. Dauncey, and John F. Bower. "C2-Alkenylation of N-heteroaromatic compounds via Brønsted acid catalysis." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5820–25. http://dx.doi.org/10.1039/c6ob00705h.

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19

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 st

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20

Grenet, Erwann, Ashis Das, Paola Caramenti, and Jérôme Waser. "Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents." Beilstein Journal of Organic Chemistry 14 (May 25, 2018): 1208–14. http://dx.doi.org/10.3762/bjoc.14.102.

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The C–H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C–H bond in bipyridinones and quinoline N-oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline N-oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups.

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21

Keith, John M. "One Step Conversion of Heteroaromatic-N-Oxides to Imidazolo-Heteroarenes." Journal of Organic Chemistry 73, no. 1 (2008): 327–30. http://dx.doi.org/10.1021/jo702038g.

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22

Balicki, Roman, and Urszula Chmielowiec. "A Mild Deoxygenation of Heteroaromatic N-Oxides by Formamidinesulfinic Acid." Monatshefte für Chemie/Chemical Monthly 131, no. 10 (2000): 1105–7. http://dx.doi.org/10.1007/s007060070044.

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23

Balicki, Roman, and Jerzy Golinski. "A Simple and Efficient Method for the Preparation of N-Heteroaromatic N-oxides." Synthetic Communications 30, no. 8 (2000): 1529–34. http://dx.doi.org/10.1080/00397910008087182.

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24

P. Andreev, Vladimir, Alexander V. Ryzhakov, and Ludmila L. Rodina. "Molecular Complexes of Heteroaromatic N-Oxides and Their Reactions with Nucleophiles." HETEROCYCLES 60, no. 2 (2003): 419. http://dx.doi.org/10.3987/com-02-9592.

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25

Wang, Hui, Yu Pei, Jie Bai, Jinli Zhang, Yangjie Wu, and Xiuling Cui. "ChemInform Abstract: Dimerization of Heteroaromatic N-Oxides under Metal-Free Conditions." ChemInform 46, no. 5 (2015): no. http://dx.doi.org/10.1002/chin.201505164.

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26

Kaczmarek, Lukasz, Marek Malinowski, and Roman Balicki. "Simple and efficient deoxygenation of heteroaromatic n-oxides using TiCl4/SnCl2." Bulletin des Sociétés Chimiques Belges 97, no. 10 (2010): 787–90. http://dx.doi.org/10.1002/bscb.19880971007.

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27

Chen, Xiaopei, Fangfang Yang, Xiuling Cui, and Yangjie Wu. "Potassium Hydroxide-Catalyzed Alkynylation of Heteroaromatic N-Oxides with Terminal Alkynes." Advanced Synthesis & Catalysis 359, no. 22 (2017): 3922–26. http://dx.doi.org/10.1002/adsc.201700931.

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28

Wang, Youliang, and Liming Zhang. "ChemInform Abstract: Recent Developments in the Chemistry of Heteroaromatic N-Oxides." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518272.

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29

Najóczki, Ferenc, Mária Szabó, Norbert Lihi, Antal Udvardy, and István Fábián. "Synthesis and Characterization of 1,10-Phenanthroline-mono-N-oxides." Molecules 26, no. 12 (2021): 3632. http://dx.doi.org/10.3390/molecules26123632.

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N-oxides of N-heteroaromatic compounds find widespread applications in various fields of chemistry. Although the strictly planar aromatic structure of 1,10-phenanthroline (phen) is expected to induce unique features of the corresponding N-oxides, so far the potential of these compounds has not been explored. In fact, appropriate procedure has not been reported for synthesizing these derivatives of phen. Now, we provide a straightforward method for the synthesis of a series of mono-N-oxides of 1,10-phenanthrolines. The parent compounds were oxidized by a green oxidant, peroxomonosulfate ion in

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30

Balicki, Roman, Lukasz Kaczmarek, and Marek Malinowski. "Selective Reduction of the N-O Bond in Heteroaromatic N-Oxides by TiCl4/SnCl2." Synthetic Communications 19, no. 5-6 (1989): 897–900. http://dx.doi.org/10.1080/00397918908051009.

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31

El-Din, Ahmed Moukhtar Nour, and Abdel-Razak M. Tawfik. "Reactions of dibenzoylacetylene with N-alkylnitrones, heteroaromatic N-oxides, and diazo and azoxy compounds." Journal of Chemical & Engineering Data 32, no. 1 (1987): 125–27. http://dx.doi.org/10.1021/je00047a036.

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32

Nemeikaitė-Čėnienė, Aušra, Jonas Šarlauskas, Lina Misevičienė, et al. "Aerobic Cytotoxicity of Aromatic N-Oxides: The Role of NAD(P)H:Quinone Oxidoreductase (NQO1)." International Journal of Molecular Sciences 21, no. 22 (2020): 8754. http://dx.doi.org/10.3390/ijms21228754.

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Derivatives of tirapazamine and other heteroaromatic N-oxides (ArN→O) exhibit tumoricidal, antibacterial, and antiprotozoal activities, which are typically attributed to bioreductive activation and free radical generation. In this work, we aimed to clarify the role of NAD(P)H:quinone oxidoreductase (NQO1) in ArN→O aerobic cytotoxicity. We synthesized 9 representatives of ArN→O with uncharacterized redox properties and examined their single-electron reduction by rat NADPH:cytochrome P-450 reductase (P-450R) and Plasmodium falciparum ferredoxin:NADP+ oxidoreductase (PfFNR), and by rat NQO1. NQO1

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33

Yamanaka, Hiroshi, Takao Sakamoto, Yoshinori Kondo, Norio Miura, and Kazuhiko Hayashi. "Condensed Heteroaromatic Ring Systems. XI. A Facile Synthesis of Isoquinoline N-Oxides." HETEROCYCLES 24, no. 8 (1986): 2311. http://dx.doi.org/10.3987/r-1986-08-2311.

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34

V. Ryzhakov, Alexander, and Ludmila L. Rodina. "Recent Trends in the Chemistry of Molecular Complexes of Heteroaromatic N-Oxides." HETEROCYCLES 75, no. 10 (2008): 2367. http://dx.doi.org/10.3987/rev-08-630.

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35

HIGUCHI, Tsunehiko. "Versatile, Highly Efficient Oxidations with Heteroaromatic N-Oxides Catalyzed by Ruthenium Porphyrin." Journal of Synthetic Organic Chemistry, Japan 53, no. 7 (1995): 633–44. http://dx.doi.org/10.5059/yukigoseikyokaishi.53.633.

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36

Puthanveedu, Mahesh, Vasiliki Polychronidou, and Andrey P. Antonchick. "Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes." Organic Letters 21, no. 9 (2019): 3407–11. http://dx.doi.org/10.1021/acs.orglett.9b01141.

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37

Hnatejko, Zbigniew. "New complexes of heteroaromatic N-oxides with europium, uranyl and zinc ions." Journal of Rare Earths 30, no. 6 (2012): 552–58. http://dx.doi.org/10.1016/s1002-0721(12)60090-8.

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38

Balsarini, Christian, Barbara Novo, and Giuseppe Resnati. "Formation of the N-oxides of heteroaromatic nitrogen compounds by perfluorinated oxaziridines." Journal of Fluorine Chemistry 80, no. 1 (1996): 31–34. http://dx.doi.org/10.1016/s0022-1139(96)03456-2.

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39

Andreev, V. P. "The effect of electronic factors on the reactivity of heteroaromatic N-oxides." Chemistry of Heterocyclic Compounds 46, no. 2 (2010): 184–95. http://dx.doi.org/10.1007/s10593-010-0490-5.

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40

NAKAGAWA, Hiroshi, Tsunehiko HIGUCHI, Kazuya KIKUCHI, Yasuteru URANO, and Tetsuo NAGANO. "Selective Deoxygenation of Heteroaromatic N-Oxides with Olefins Catalyzed by Ruthenium Porphyrin." CHEMICAL & PHARMACEUTICAL BULLETIN 46, no. 10 (1998): 1656–57. http://dx.doi.org/10.1248/cpb.46.1656.

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41

Balicki, Roman, and Urszula Chmielowiec. "ChemInform Abstract: A Mild Deoxygenation of Heteroaromatic N-Oxides by Formamidinesulfinic Acid." ChemInform 32, no. 6 (2001): no. http://dx.doi.org/10.1002/chin.200106074.

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42

SINHA, N., and R. SINHA. "ChemInform Abstract: Rearrangement of Heteroaromatic N-Oxides. A New Synthesis of Chloromethylquinoline." ChemInform 27, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199647144.

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43

Balicki, Roman, and Jerzy Golinski. "ChemInform Abstract: A Simple and Efficient Method for the Preparation of N-Heteroaromatic N-Oxides." ChemInform 31, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.200034053.

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44

Kaur, Ramandeep, Sudip Mandal, Debolina Banerjee та Ashok Kumar Yadav. "Transition Metal Free α −C−H Functionalization of Six Membered Heteroaromatic‐ N ‐Oxides". ChemistrySelect 6, № 12 (2021): 2832–54. http://dx.doi.org/10.1002/slct.202100319.

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45

Pietraszkiewicz, Marek, Jerzy Karpiuk, and Oksana Pietraszkiewicz. "Macrocyclic and macropolycyclic heteroaromatic N-oxides: powerful sensitizers for the lanthanide ions emission." Journal of Alloys and Compounds 300-301 (April 2000): 141–46. http://dx.doi.org/10.1016/s0925-8388(99)00745-8.

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46

Su, Yuan, Xuejun Zhou, Chunlian He, Wei Zhang, Xiao Ling, and Xia Xiao. "In Situ Generated HypoIodite Activator for the C2 Sulfonylation of Heteroaromatic N-oxides." Journal of Organic Chemistry 81, no. 12 (2016): 4981–87. http://dx.doi.org/10.1021/acs.joc.6b00475.

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47

Sheinker, V. N., A. D. Garnovsky, E. G. Merinova, V. S. Troilina, O. A. Osipov, and A. P. Sadimenko. "Spectral investigation of complex-formation of heteroaromatic N-oxides with tetracyanoethylene in solutions." Journal of Molecular Structure 143 (March 1986): 395–98. http://dx.doi.org/10.1016/0022-2860(86)85284-x.

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48

Nizhnik, Yakov P., Alex Sons, Matthias Zeller, and Sergiy V. Rosokha. "Effects of Supramolecular Architecture on Halogen Bonding between Diiodine and Heteroaromatic N-Oxides." Crystal Growth & Design 18, no. 2 (2018): 1198–207. http://dx.doi.org/10.1021/acs.cgd.7b01734.

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49

BALICKI, R., and L. KACZMAREK. "ChemInform Abstract: Simple and Convenient Deoxygenation of Heteroaromatic N-Oxides with Sodium Hypophosphite." ChemInform 26, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199523139.

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50

Hanusek, Jiří, and Vladimír Macháček. "Intramolecular base-catalyzed reactions involving interaction between benzene nitro groups and ortho carbon chains." Collection of Czechoslovak Chemical Communications 74, no. 5 (2009): 811–33. http://dx.doi.org/10.1135/cccc2008216.

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The review is focused on the understanding of processes involving chemical interaction between benzene nitro group and ortho carbon chain containing heteroatom (N, O, S) adjacent to the ring. In most cases these compounds undergo base-catalyzed cyclization to give heteroaromatic N-oxides that can be subsequently transformed to related heterocycles under the same conditions. However, in some cases, depending on substitution of the benzene ring, side chain or the base used, the formation of other compounds – both heterocyclic and non-heterocyclic such as nitroso and azoxy compounds, spiro Meisen

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