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Journal articles on the topic 'Nitroquinolines'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Szpakiewicz, Barbara, and Maria Grzegożek. "Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole." Canadian Journal of Chemistry 86, no. 7 (2008): 682–85. http://dx.doi.org/10.1139/v08-051.

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3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substi

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2

Wantulok, Jakub, Daniel Swoboda, Jacek E. Nycz, et al. "Direct Amination of Nitroquinoline Derivatives via Nucleophilic Displacement of Aromatic Hydrogen." Molecules 26, no. 7 (2021): 1857. http://dx.doi.org/10.3390/molecules26071857.

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The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-y

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3

Woźniak, Marian, and Maria Grzegożek. "Oxidative Methylamination of Nitroquinolines." Liebigs Annalen der Chemie 1993, no. 8 (1993): 823–29. http://dx.doi.org/10.1002/jlac.1993199301130.

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4

WOZNIAK, M., and M. GRZEGOZEK. "ChemInform Abstract: Oxidative Methylamination of Nitroquinolines." ChemInform 24, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199348089.

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5

Skolyapova, Alexandrina D., Galina A. Selivanova, Evgeny V. Tretyakov, Irina Yu Bagryanskaya, and Vitalij D. Shteingarts. "Synthesis of polyfluorinated aminoquinolines via nitroquinolines." Journal of Fluorine Chemistry 211 (July 2018): 14–23. http://dx.doi.org/10.1016/j.jfluchem.2018.04.006.

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6

Luque-Agudo, V., José M. Padrón, E. Román, J. A. Serrano, and M. V. Gil. "Antiproliferative activity of new 2-glyco-3-nitro-1,2-dihydroquinolines and quinolines synthesized under solventless conditions promoted by neutral alumina." New Journal of Chemistry 42, no. 22 (2018): 18342–47. http://dx.doi.org/10.1039/c8nj03372b.

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This paper describes the syntheses of new 2-glyco-3-nitro-1,2-dihydroquinolines and 2-glyco-3-nitroquinolines by one-pot aza-Michael–Henry-dehydration reactions using green procedures, as well as the evaluation of their antiproliferative activity.

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7

Glushkov, R. G., and N. K. Davydova. "Chemistry of 3-nitroquinolines and their derivatives (review)." Pharmaceutical Chemistry Journal 26, no. 4 (1992): 325–37. http://dx.doi.org/10.1007/bf00773165.

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8

Fabian, Walter. "Zur Interpretation des Substituenteneinflusses auf das UV-spektroskopische Verhalten von Chinolinderivaten." Zeitschrift für Naturforschung A 40, no. 7 (1985): 719–25. http://dx.doi.org/10.1515/zna-1985-0712.

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The results of PPP calculations on the seven isomeric amino- as well as nitroquinolines (chosen as models for donator and acceptor substituted derivatives) are analyzed by means of configuration analysis. Based on these analyses the characteristic dependence of the UV spectra of these compounds on the position and nature of the substituent is interpreted and verified using a simplified molecules-in-molecule calculation.

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9

Grzegożek, Maria. "Vicarious nucleophilic amination of nitroquinolines by 1,1,1-trimethylhydrazinium iodide." Journal of Heterocyclic Chemistry 45, no. 6 (2008): 1879–82. http://dx.doi.org/10.1002/jhet.5570450652.

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10

Tondys, Hanna, Henk C. van der Plas, and Marian Woźniak. "On the chichibabin amination of quinoline and some nitroquinolines." Journal of Heterocyclic Chemistry 22, no. 2 (1985): 353–55. http://dx.doi.org/10.1002/jhet.5570220226.

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11

GLUSHKOV, R. G., and N. K. DAVYDOVA. "ChemInform Abstract: Chemistry of 3-Nitroquinolines and Their Derivatives." ChemInform 23, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199249324.

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12

Zhou, Yu, Jian Li, Hong Liu, Linxiang Zhao, and Hualiang Jiang. "An unusual de-nitro reduction of 2-substituted-4-nitroquinolines." Tetrahedron Letters 47, no. 48 (2006): 8511–14. http://dx.doi.org/10.1016/j.tetlet.2006.09.140.

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13

Grzegożek, Maria, Marian Woźniak, and Henk C. van der Plas. "Regioselectivity in SNH Reactions of Nitroquinolines with Chloromethyl Phenyl Sulfone." Liebigs Annalen 1996, no. 4 (2006): 641–44. http://dx.doi.org/10.1002/jlac.199619960426.

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14

Saeki, Ken-ichi, Ryuichi Murakami, Arihiro Kohara, et al. "Substituent effect of a fluorine atom on the mutagenicity of nitroquinolines." Mutation Research/Genetic Toxicology and Environmental Mutagenesis 441, no. 2 (1999): 205–13. http://dx.doi.org/10.1016/s1383-5718(99)00049-2.

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15

Li, Hai-hong, He Huang, Xiu-hua Zhang, et al. "Discovering novel 3-nitroquinolines as a new class of anticancer agents." Acta Pharmacologica Sinica 29, no. 12 (2008): 1529–38. http://dx.doi.org/10.1111/j.1745-7254.2008.00907.x.

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16

Urzúa, Julio, Claudia Yañez, José Carbajo, and Juan A. Squella. "Substituted Nitroquinolines Immobilized in Multiwalled Carbon Nanotubes: An Unconventional Voltammetric Experiment." Journal of The Electrochemical Society 165, no. 16 (2018): G176—G181. http://dx.doi.org/10.1149/2.0391816jes.

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17

Rode, Navnath, Antonio Arcadi, Marco Chiarini та Fabio Marinelli. "An Improved Environmentally Friendly Approach to 4-Nitro-, 4-Sulfonyl-, and 4-Aminoquinolines and 4-Quinolones through Conjugate Addition of Nucleophiles to β-(2-Aminophenyl)-α,β-ynones". Synthesis 49, № 11 (2017): 2501–12. http://dx.doi.org/10.1055/s-0036-1588147.

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Sequential addition/annulation reactions of sulfinate and nitrite anions to β-(2-aminophenyl)-α,β-ynones led to valuable 4-sulfonylquinolines and 4-nitroquinolines. The latter proved to be versatile precursors of N-unsubstituted 4-aminoquinolines and 4-quinolones. Reaction of β-(2-aminophenyl)-α,β-ynones with DMF/NaOH resulted in the formation of 4-(dimethylamino)quinolines. The use of an alternative CO-free procedure for the preparation of substrates β-(2-aminophenyl)-α,β-ynones allowed extension of the methodology to the synthesis of 4-substituted 2-alkylquinolines.

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18

Bastrakov, Maxim A., Alexey M. Starosotnikov, Vadim V. Kachala, Ivan V. Fedyanin, and Svyatoslav A. Shevelev. "Facile Dearomatization of Nitroquinolines through [3+2] and [4+2] Cycloaddition Reactions." Asian Journal of Organic Chemistry 4, no. 2 (2015): 146–53. http://dx.doi.org/10.1002/ajoc.201402207.

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19

GRZEGOZEK, M., M. WOZNIAK, and H. C. VAN DER PLAS. "ChemInform Abstract: Regioselectivity in SNH Reactions of Nitroquinolines with Chloromethyl Phenyl Sulfone." ChemInform 27, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199632185.

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20

Arasakumar, Thangaraj, Sadasivam Mathusalini, Subashini Gopalan, Selvaraj Shyamsivappan, Athar Ata, and Palathurai Subramaniam Mohan. "Biologically active perspective synthesis of heteroannulated 8-nitroquinolines with green chemistry approach." Bioorganic & Medicinal Chemistry Letters 27, no. 7 (2017): 1538–46. http://dx.doi.org/10.1016/j.bmcl.2017.02.042.

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21

Wright, Jon, Gary Bolton, Mark Creswell, et al. "8-amino-6-(arylsulphonyl)-5-nitroquinolines: novel nonpeptide neuropeptide Y1 receptor antagonists." Bioorganic & Medicinal Chemistry Letters 6, no. 15 (1996): 1809–14. http://dx.doi.org/10.1016/0960-894x(96)00319-8.

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22

Chauhan, Monika, Anil Rana, Jimi Marin Alex, Arvind Negi, Sandeep Singh, and Raj Kumar. "Design, microwave-mediated synthesis and biological evaluation of novel 4-aryl(alkyl)amino-3-nitroquinoline and 2,4-diaryl(dialkyl)amino-3-nitroquinolines as anticancer agents." Bioorganic Chemistry 58 (February 2015): 1–10. http://dx.doi.org/10.1016/j.bioorg.2014.11.004.

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23

WRIGHT, J., G. BOLTON, M. CRESWELL, et al. "ChemInform Abstract: 8-Amino-6-(arylsulfonyl)-5-nitroquinolines: Novel Nonpeptide Neuropeptide Y1 Receptor Antagonists." ChemInform 27, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199649267.

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24

Jiranek, Ivan, Karolina Peckova, Zuzana Kralova, Josino C. Moreira, and Jiri Barek. "The use of silver solid amalgam electrode for voltammetric and amperometric determination of nitroquinolines." Electrochimica Acta 54, no. 7 (2009): 1939–47. http://dx.doi.org/10.1016/j.electacta.2008.08.022.

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25

Demidov, Oleg P., Diana Yu Pobedinskaya, Elena K. Avakyan, Gulminat A. Amangasieva, and Ivan V. Borovlev. "S N H Arylamination of Nitroquinolines: Access to Nitro and Nitroso Derivatives of Arylaminoquinolines." Chemistry of Heterocyclic Compounds 54, no. 9 (2018): 875–86. http://dx.doi.org/10.1007/s10593-018-2368-x.

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26

Amangasieva, Gulminat А., Elena K. Avakyan, Oleg P. Demidov, Anastasia A. Borovleva, Diana Yu Pobedinskaya, and Ivan V. Borovlev. "SNH Amidation of nitroquinolines: synthesis of amides on the basis of nitro- and nitrosoquinolines." Chemistry of Heterocyclic Compounds 55, no. 7 (2019): 623–31. http://dx.doi.org/10.1007/s10593-019-02508-3.

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27

Bastrakov, Maxim A., Alexey M. Starosotnikov, Vadim V. Kachala, Ivan V. Fedyanin, and Svyatoslav A. Shevelev. "ChemInform Abstract: Facile Dearomatization of Nitroquinolines Through [3 + 2] and [4 + 2] Cycloaddition Reactions." ChemInform 46, no. 27 (2015): no. http://dx.doi.org/10.1002/chin.201527034.

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28

Kawakami, Takehiko, and Hitomi Suzuki. "Direct thioalkylation of nitroquinolines with alkanethiolate anions via nucleophilic displacement of a ring hydrogen atom." Journal of the Chemical Society, Perkin Transactions 1, no. 21 (2000): 3640–44. http://dx.doi.org/10.1039/b004190o.

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29

Denny, William A., Graham J. Atwell, Peter B. Roberts, et al. "Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins." Journal of Medicinal Chemistry 35, no. 26 (1992): 4832–41. http://dx.doi.org/10.1021/jm00104a008.

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30

Laschat, Sabine, Philipp Seubert, Marcel Freund, et al. "Buchwald–Hartwig versus Microwave-Assisted Amination of Chloroquinolines: En Route to the Pyoverdin Chromophore." Synlett 31, no. 12 (2020): 1177–81. http://dx.doi.org/10.1055/s-0040-1707810.

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The reaction of 2-chloro-6,7-dimethoxy-3-nitroquinoline with a series of amines and aminoalkanoates under basic microwave-mediated conditions and under Buchwald–Hartwig amination conditions is reported. The microwave irradiation favored the reaction with amines, resulting in yields of up to 80%, whereas amino acid functionalization gave yields comparable to those of Buchwald–Hartwig amination. tert-Butyl (2R)-4-[(6,7-dimethoxy-3-nitroquinolin-2-yl)amino]-2-hydroxybutanoate was successfully cyclized to the pyoverdin chromophore, a subunit of siderophores.

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31

Anderson, Robert F., William A. Denny, William R. Wilson, and Kantilal B. Patel. "Pulse radiolysis studies on the oxidation of OH? radical-damaged DNA by nitroquinolines in aqueous solution." Journal of the Chemical Society, Faraday Transactions 91, no. 14 (1995): 2115. http://dx.doi.org/10.1039/ft9959102115.

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32

Cai, Xian-Feng, Mu-Wang Chen, Zhi-Shi Ye, et al. "Asymmetric Transfer Hydrogenation of 3-Nitroquinolines: Facile Access to Cyclic Nitro Compounds with Two Contiguous Stereocenters." Chemistry - An Asian Journal 8, no. 7 (2013): 1381–85. http://dx.doi.org/10.1002/asia.201300380.

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33

KAIYA, TOYO, NAOHIRO SHIRAI, and YUTAKA KAWAZOE. "Proton and carbon-13 nuclear magnetic resonance chemical shift data for nitroquinolines and their N-oxides." CHEMICAL & PHARMACEUTICAL BULLETIN 34, no. 2 (1986): 881–85. http://dx.doi.org/10.1248/cpb.34.881.

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34

Kawakami, Takehiko, and Hitomi Suzuki. "ChemInform Abstract: Direct Thioalkylation of Nitroquinolines with Alkanethiolate Anions via Nucleophilic Displacement of a Ring Hydrogen Atom." ChemInform 32, no. 12 (2001): no. http://dx.doi.org/10.1002/chin.200112149.

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35

Cai, Xian-Feng, Mu-Wang Chen, Zhi-Shi Ye, et al. "ChemInform Abstract: Asymmetric Transfer Hydrogenation of 3-Nitroquinolines: Facile Access to Cyclic Nitro Compounds with Two Contiguous Stereocenters." ChemInform 44, no. 46 (2013): no. http://dx.doi.org/10.1002/chin.201346146.

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36

Maślankiewicz, Andrzej, Magdalena Kosiecka, and Maria J. Maslankiewicz. "4-Substituted 3-Methylsulfanyl-5-, 6-, and 8-nitroquinolines from Nitro Derivatives of 4-Substituted 3’-Methylsulfinyl-3,4’-diquinolinyl Sulfides." HETEROCYCLES 65, no. 7 (2005): 1577. http://dx.doi.org/10.3987/com-05-10370.

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37

Mitrović, Ana, Bojana Mirković, Izidor Sosič, Stanislav Gobec, and Janko Kos. "Inhibition of endopeptidase and exopeptidase activity of cathepsin B impairs extracellular matrix degradation and tumour invasion." Biological Chemistry 397, no. 2 (2016): 165–74. http://dx.doi.org/10.1515/hsz-2015-0236.

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Abstract Cathepsin B is a lysosomal cysteine protease that is implicated in a number of physiological processes, including protein turnover in lysosomes. Changes in its expression are associated with a variety of pathological processes, including cancer. Due to the structural feature, termed the occluding loop, cathepsin B differs from other cysteine proteases in possessing both, endopeptidase and exopeptidase activity. Here we investigated the impact of both cathepsin B activities on intracellular and extracellular collagen IV degradation and tumour cell invasion using new selective synthetic

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38

Sánchez, Juan Domingo, Riccardo Egris, Subbu Perumal, Mercedes Villacampa, and J. Carlos Menéndez. "Aryl Grignard Reagents in Chemodivergent N- and C-Arylations: Concise Access to Two Families of Tetracyclic Fused Carbazoles from 6-Nitroquinolines." European Journal of Organic Chemistry 2012, no. 12 (2012): 2375–85. http://dx.doi.org/10.1002/ejoc.201101848.

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39

Suzuki, Hitomi, and Takehiko Kawakami. "Straightforward Synthesis of Some 2- or 3-Substituted Naphtho- and Quinolino[1,2,4]triazines via the Cyclocondensation of Nitronaphthalenes and Nitroquinolines with Guanidine Base." Journal of Organic Chemistry 64, no. 9 (1999): 3361–63. http://dx.doi.org/10.1021/jo982139m.

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40

Sanchez, Juan Domingo, Riccardo Egris, Subbu Perumal, Mercedes Villacampa, and J. Carlos Menendez. "ChemInform Abstract: Aryl Grignard Reagents in Chemodivergent N- and C-Arylations: Concise Access to Two Families of Tetracyclic Fused Carbazoles from 6-Nitroquinolines." ChemInform 43, no. 36 (2012): no. http://dx.doi.org/10.1002/chin.201236146.

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41

Chinh, Pham The, Pham Thi Tham, Duong Huong Quynh, et al. "Synthesis and Cytotoxic Activity of Several Novel N-Alkyl-Plinabulin Derivatives With Aryl Group Moieties." Natural Product Communications 16, no. 4 (2021): 1934578X2110100. http://dx.doi.org/10.1177/1934578x211010040.

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Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), a

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42

Wozniak, Marian, Andrzej Baranski, and Krystyna Nowak. ".sigma.-Adduct formation between azines and liquid ammonia. 47. Frontier orbital interactions in the regioselectivity of the amination of nitroquinolines by liquid ammonia/potassium permanganate." Journal of Organic Chemistry 52, no. 26 (1987): 5643–46. http://dx.doi.org/10.1021/jo00235a001.

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43

Suzuki, Hitomi, and Takehiko Kawakami. "ChemInform Abstract: Straightforward Synthesis of Some 2- or 3-Substituted Naphtho- and Quinolino[1,2,4]triazines via the Cyclocondensation of Nitronaphthalenes and Nitroquinolines with Guanidine Base." ChemInform 30, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199933178.

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44

Yan, Ming-Chung, Zhijay Tu, Chunchi Lin, Shengkai Ko, Jianming Hsu, and Ching-Fa Yao. "An Investigation of the Reaction of 2-Aminobenzaldehyde Derivatives with Conjugated Nitro-olefins: An Easy and Efficient Synthesis of 3-Nitro-1,2-dihydroquinolines and 3-Nitroquinolines." Journal of Organic Chemistry 69, no. 5 (2004): 1565–70. http://dx.doi.org/10.1021/jo030070z.

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45

Xu, Liang, Bao-Li Xu, Shu-Jun Lu, Bing Wang, and Ting-Guo Kang. "8-Nitroquinoline." Acta Crystallographica Section E Structure Reports Online 67, no. 4 (2011): o957. http://dx.doi.org/10.1107/s1600536811010014.

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46

Lynch, Daniel E., Graham Smith, Karl A. Byriel, and Colin H. L. Kennard. "Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes." Australian Journal of Chemistry 50, no. 10 (1997): 977. http://dx.doi.org/10.1071/c97067.

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A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)(C9H6N2O2)], 4-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)2(C9H6N2O2)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C7H7NO2)(C9H6N2O2)] and 4-aminobenzoic acid with 5-

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47

Stanley, J. S., and A. M. Benson. "The conjugation of 4-nitroquinoline 1-oxide, a potent carcinogen, by mammalian glutathione transferases. 4-Nitroquinoline 1-oxide conjugation by human, rat and mouse liver cytosols, extrahepatic organs of mice and purified mouse gluthathione tranferase isoenzymes." Biochemical Journal 256, no. 1 (1988): 303–6. http://dx.doi.org/10.1042/bj2560303.

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The conjugation of 4-nitroquinoline 1-oxide with GSH by human, rat and mouse liver cytosols, by purified mouse GSH transferases and by extrahepatic organ cytosols of male and female mice was investigated. 4-Nitroquinoline 1-oxide was as effectively conjugated by human liver cytosol as was 1-chloro-2,4-dinitrobenzene, at a substrate concentration of 0.1 mM. Mouse isoenzymes composed of Yb1 and Yf subunits exhibited high activity towards 4-nitroquinoline 1-oxide. Human, rat and mouse hepatic activities towards this substrate correlated with the hepatic isoenzyme compositions.

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48

Sawada, Yosuke, Reiko Fujii, Ikuo Igami, Atsushi Kawai, Teruo Kamiki, and Makoto Niwaf. "Endotoxin removal from water using microporous polyethylene chopped fibres as a new adsorbent." Journal of Hygiene 97, no. 1 (1986): 103–14. http://dx.doi.org/10.1017/s0022172400064391.

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SUMMARYA new adsorbent, microporous polyethylene chopped fibre, was produced from a high density polyethylene. This can adsorb lipopolysaccharides (LPS) linearly up to 2 h, and showed the highest capacity to adsorb LPS when compared with two other polyethylene-based adsorbents and a polystyrene-based adsorbent. More than twice as much orange II and 4-nitroquinoline N oxide were adsorbed in the new adsorbent as was LPS. The adsorption isotherm of the new adsorbent for LPS was of Ln type, the correlation between adsorption and concentration of solute was proportional; whereas orange II and 4-nit

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49

Gotoh, Kazuma, and Hiroyuki Ishida. "Crystal structures of the two isomeric hydrogen-bonded cocrystals 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1) and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1)." Acta Crystallographica Section E Crystallographic Communications 75, no. 11 (2019): 1694–99. http://dx.doi.org/10.1107/s2056989019013896.

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The structures of two isomeric compounds of 5-nitroquinoline with chloro- and nitro-substituted benzoic acid, namely, 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1), (I), and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), (II), both C7H4ClNO4·C9H6N2O2, have been determined at 190 K. In each compound, the acid and base molecules are held together by an O—H...N hydrogen bond. In the crystal of (I), the hydrogen-bonded acid–base units are linked by a C—H...O hydrogen bond, forming a tape structure along [1\overline{2}0]. The tapes are stacked into a layer parallel to the ab plane via N

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50

Mąkosza, Mieczyslaw, Andrzej Kinowski, Witold Danikiewicz, and Boguslaw Mudryk. "Vicarious Nucleophilic Substitution in Nitroquinolines1)." Liebigs Annalen der Chemie 1986, no. 1 (1986): 69–77. http://dx.doi.org/10.1002/jlac.198619860107.

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