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Journal articles on the topic '2-aminobenzonitrile'

Author: Grafiati

Published: 27 February 2024

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1

Ru, Zong-Ling, and Guo-Xi Wang. "Bis(2-aminobenzonitrile)tetraaquacobalt(II) dichloride." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 28, 2009): m1688. http://dx.doi.org/10.1107/s1600536809050272.

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2

Marinho, Elina, and M. Proença. "The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines." Synthesis 47, no. 11 (March 17, 2015): 1623–32. http://dx.doi.org/10.1055/s-0034-1380322.

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2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

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3

Sheng, Zhi-Zheng, Min-Min Huang, Teng Xue, Fei Xia, and Hai-Hong Wu. "Alcohol amine-catalyzed CO2 conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water." RSC Advances 10, no. 57 (2020): 34910–15. http://dx.doi.org/10.1039/d0ra06439d.

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Commercial DEA is proposed for efficiently promoting the cyclization of CO₂ and 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione (up to 94% yield) while water acts as the solvent and co-catalyst.

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4

Fuster, Marta G., Imane Moulefera, Mercedes G. Montalbán, José Pérez, Gloria Víllora, and Gabriel García. "Synthesis and Characterization of New Ruthenium (II) Complexes of Stoichiometry [Ru(p-Cymene)Cl2L] and Their Cytotoxicity against HeLa-Type Cancer Cells." Molecules 27, no. 21 (October 26, 2022): 7264. http://dx.doi.org/10.3390/molecules27217264.

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When the [Ru(p-cymene)(μ-Cl)Cl]2 complex is made to react, in dichloromethane, with the following ligands: 2-aminobenzonitrile (2abn), 4-aminobenzonitrile (4abn), 2-aminopyridine (2ampy) and 4-aminopyridine (4ampy), after addition of hexane, the following compounds are obtained: [Ru(p-cymene)Cl2(2abn)] (I), [Ru(p-cymene)Cl2(4abn)] (II), [Ru(p-cymene)Cl2(2ampy] (III) and [Ru(p-cymene)Cl2(μ-(4ampy)] (IV). All the compounds are characterized by elemental analysis of carbon, hydrogen and nitrogen, proton nuclear magnetic resonance, COSY 1H-1H, high-resolution mass spectrometry (ESI), thermogravimetry and single-crystal X-ray diffraction (the crystal structure of III is reported and compared with the closely related literature of II). The cytotoxicity effects of complexes were described for cervical cancer HeLa cells via 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide (MTT) assay. The results demonstrate a low in vitro anticancer potential of the complexes.

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5

Boukthir, Mona, Fathi Zribi, Mohamed Belhouchet, and Fakher Chabchoub. "A Facile Synthesis of Pyrimidoquinazoline Derivatives." JOURNAL OF ADVANCES IN CHEMISTRY 7, no. 3 (December 17, 2011): 1434–39. http://dx.doi.org/10.24297/jac.v7i3.2379.

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A series of pyrimidoquinazoline are prepared via the reaction of ethyl 2,2-dicyano-1-arylvinylcarbamate derivatives 1a-b with methyl 2-aminobenzoate, 1-(2-aminophenyl)ethanone and 2-aminobenzonitrile. The reactivity of compounds 1a-b toward 3-amino-4,6-diphénylnicotinonitrile are studied. The structures of the synthesized compounds are elucidated by X-ray diffraction, IR spectroscopy and nuclear magnetic resonance.

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6

Ahuja, I. S., and Shailendra Tripathi. "X-ray diffraction studies on dichloro-(2-aminobenzonitrile)copper(II)." Crystal Research and Technology 25, no. 6 (June 1990): K130—K132. http://dx.doi.org/10.1002/crat.2170250623.

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7

Lang, Xian-Dong, Shuai Zhang, Qing-Wen Song, and Liang-Nian He. "Tetra-butylphosphonium arginine-based ionic liquid-promoted cyclization of 2-aminobenzonitrile with carbon dioxide." RSC Advances 5, no. 20 (2015): 15668–73. http://dx.doi.org/10.1039/c4ra16057f.

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Tetra-butylphosphonium arginine-based IL able to activate both amino-groups and CO₂ proved to be an efficient and recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from 2-aminobenzonitriles and CO₂ under solvent-free conditions.

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8

Brodersen, Klaus, and Jürgen Hofmann. "Synthese und Kristallstruktur von Bis(o-aminobenzonitril)-diquecksilber(I)-dinitrat / Synthesis and Crystal Structure of Bis(o-aminobenzonitrile)dimercury(I)-dinitrate." Zeitschrift für Naturforschung B 46, no. 12 (December 1, 1991): 1684–88. http://dx.doi.org/10.1515/znb-1991-1217.

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[Hg2(o-NH2C6H4CN)2](NO3)2 is formed by the reaction of o-aminobenzonitrile with dimercury(I)-dinitrate in methanol. It crystallizes in the monoclinic space group P 2/c with a = 8.6819(5)Å, b = 5.3696(6)Å, c = 19.7645(8)Å, β = 95.138(12)° and Ζ = 2. The crystal structure has been determined by single crystal X-ray diffraction with applied gaussian absorption correction and refined to an Rw-value of 0.027.The Hg22+-ion is coordinated to both amino nitrogen atoms. Strong hydrogen bonds and bridging nitrate ions lead to chain structure.

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9

Jonathan Fray, M., Paul Allen, Paul R. Bradley, Clare E. Challenger, Michael Closier, Tim J. Evans, Mark L. Lewis, et al. "Synthesis of 5-Heterocyclic Substituted Quinazolin-4-ones via 2-Aminobenzonitrile Derivatives." HETEROCYCLES 67, no. 2 (2006): 489. http://dx.doi.org/10.3987/com-05-s(t)17.

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10

Moitsheki, Lesego J., Susan A. Bourne, and Luigi R. Nassimbeni. "catena-Poly[[bis(thiocyanato-κN)cobalt(II)]-di-μ-2-aminobenzonitrile-κ2N,N′]." Acta Crystallographica Section E Structure Reports Online 61, no. 12 (November 16, 2005): m2580—m2581. http://dx.doi.org/10.1107/s1600536805036846.

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11

Sun, Di, Fu-Jing Liu, Hong-Jun Hao, Yun-Hua Li, Rong-Bin Huang, and Lan-Sun Zheng. "Six low-dimensional silver(I) coordination complexes derived from 2-aminobenzonitrile and carboxylates." Inorganica Chimica Acta 387 (May 2012): 271–76. http://dx.doi.org/10.1016/j.ica.2012.01.027.

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12

Brodersen, Klaus, and Jürgen Hofmann. "Synthese und Kristallstruktur von Bis(m-aminobenzonitril)- diquecksilber(I)-dinitrat/Synthesis and Crystal Structure of Bis(m-aminobenzonitrile)dimercury(I)-dinitrate." Zeitschrift für Naturforschung B 47, no. 4 (April 1, 1992): 460–64. http://dx.doi.org/10.1515/znb-1992-0402.

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The structure of bis(m-aminobenzonitrile)dimercury(I) dinitrate, [Hg2(m -NH2C6H4CN)2](NO3)2 has been determined by single crystal X-ray diffraction techniques and refined to an Rw-value of 0.022. The crystals are triclinic, space group P1 with a = 5.4878(1) Å, b = 8.4085(1) Å, c = 9.6062(1) Å, α = 92.599(3)°, β = 94.763(3)°, γ = 89.614(3)° and Z = 1.The Hg22+-ion [Hg-Hg 2.524(1) Å] is approximately axially coordinated to amino nitrogen atoms [Hg - N 2.209(4) Å, Hg - Hg - N 169.5(3)°]. Additional amino hydrogen bonds to oxygen are building chains along the b-axis containing units of L - Hg - Hg - L groups.

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13

Szczepankiewicz, Wojciech, Jerzy Suwiński, and Robert Bujok. "Synthesis of 4-Arylaminoquinazolines and 2-Aryl-4-arylaminoquinazolines from 2-Aminobenzonitrile, Anilines and Formic Acid or Benzaldehydes." Tetrahedron 56, no. 47 (November 2000): 9343–49. http://dx.doi.org/10.1016/s0040-4020(00)00899-1.

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14

Faizi, Md Serajul Haque, Emine Berrin Cinar, Alev Sema Aydin, Erbil Agar, Necmi Dege, and Ashraf Mashrai. "Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile." Acta Crystallographica Section E Crystallographic Communications 76, no. 8 (July 3, 2020): 1195–200. http://dx.doi.org/10.1107/s2056989020008907.

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The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intramolecular O—H...N hydrogen bond that forms an S(6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the a axis. C—H...π interactions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H...H and C...H/H...C interactions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is given.

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15

Zhao, Guo-Ying, Ling-Ling Mu, Latif Ullah, Meng Wang, Hong-Ping Li, and Xin-Xin Guan. "CO2 involved synthesis of quinazoline-2,4(1H,3H)-diones in water using melamine as a thermoregulated catalyst." Canadian Journal of Chemistry 97, no. 3 (March 2019): 212–18. http://dx.doi.org/10.1139/cjc-2017-0705.

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In this study, pharmaceutically relevant quinazoline-2,4(1H,3H)-diones were synthesized eco-efficiently by cycloaddition of CO2 and 2-aminobenzonitrile in water, catalyzed by melamine as a thermoregulated catalyst. Quinazoline-2,4(1H,3H)-dione was produced selectively with 92% yield at 120 °C, 4.2 MPa, and automatically separated from the hot catalytic aqueous solution, which was reused directly for several runs until its activity decreased in an obvious manner. Then, the catalyst melamine was recrystallized from the spent aqueous solution via simple cooling and reused for another several catalytic runs. The efficient valorization of CO2 and the straightforward stepwise recovery of the products and catalyst were important to save energy and minimize process waste for the practical industrial production.

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16

Zhen, Bin, Qingze Jiao, Yaping Zhang, Qin Wu, Hansheng Li, Daxin Shi, and Jiarong Li. "Fast condensation of cyclohexanone with 2-aminobenzonitrile at room temperature catalysed by an N-heterocyclic carbene." Catalysis Communications 32 (February 2013): 1–4. http://dx.doi.org/10.1016/j.catcom.2012.11.029.

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17

Lang, Xian-Dong, Shuai Zhang, Qing-Wen Song, and Liang-Nian He. "ChemInform Abstract: Tetra-Butylphosphonium Arginine-Based Ionic Liquid-Promoted Cyclization of 2-Aminobenzonitrile with Carbon Dioxide." ChemInform 46, no. 28 (June 25, 2015): no. http://dx.doi.org/10.1002/chin.201528229.

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18

Xu, Liguo, Taotao Zhou, Min Liao, Rongrong Hu, and Ben Zhong Tang. "Multicomponent Polymerizations of Alkynes, Sulfonyl Azides, and 2-Hydroxybenzonitrile/2-Aminobenzonitrile toward Multifunctional Iminocoumarin/Quinoline-Containing Poly(N-sulfonylimine)s." ACS Macro Letters 8, no. 2 (January 9, 2019): 101–6. http://dx.doi.org/10.1021/acsmacrolett.8b00884.

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19

Patil, Siddappa A., Phillip A. Medina, Seth Dever, Joseph W. Ziller, and Bradley D. Fahlman. "Influence of Reactant 4-Aminobenzonitrile Inclusion on the Crystal Structure of (Z)-4-(4-oxopent-2-en-2-ylamino)benzonitrile." Journal of Chemical Crystallography 44, no. 2 (November 29, 2013): 82–88. http://dx.doi.org/10.1007/s10870-013-0486-y.

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20

Szczepankiewicz, Wojciech, Jerzy Suwinski, and Robert Bujok. "ChemInform Abstract: Synthesis of 4-Arylaminoquinazolines and 2-Aryl-4-arylaminoquinazolines from 2-Aminobenzonitrile, Anilines and Formic Acid or Benzaldehydes." ChemInform 32, no. 13 (March 27, 2001): no. http://dx.doi.org/10.1002/chin.200113145.

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21

Aydin, Fatma, and N. Burcu Arslan. "Synthesis, Crystal Structure and Cyclic Voltammetric Behavior of N-aroyl-N′-(4′-cyanophenyl)thioureas." Molbank 2022, no. 1 (January 14, 2022): M1316. http://dx.doi.org/10.3390/m1316.

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Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonitrile. The structure of the prepared compounds was characterized by elemental analysis and FT-IR, 1H, and 13C-NMR spectroscopic methods. The crystal structure of the title compound 1 was determined by an X-ray single-crystal technique and an intramolecular C=O…H-N hydrogen bond and intermolecular C=S…H-N and C=S…H-C hydrogen interactions, which were observed for the crystal structure. The molecular electrostatic potential (MEP) and the Mulliken atomic charges of title compounds 1 and 2 were theoretically calculated and interpreted. Cyclic voltammetric (CV) experiments for the compounds were performed with the glassy carbon electrode. The reduction in potential values of the different functional groups such as nitro and cyano in title compounds were investigated using CV curves.

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22

Yan, Chao, Ying Ren, Jian-Feng Jia, and Hai-Shun Wu. "Mechanism of the chemical fixation of carbon dioxide with 2-aminobenzonitrile catalyzed by cesium carbonate: A computational study." Molecular Catalysis 432 (May 2017): 172–86. http://dx.doi.org/10.1016/j.mcat.2017.02.015.

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23

Li, Weiyi, Na Yang, and Yajing Lyu. "A mechanistic study on guanidine-catalyzed chemical fixation of CO2 with 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione." Organic Chemistry Frontiers 3, no. 7 (2016): 823–35. http://dx.doi.org/10.1039/c6qo00085a.

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24

Fujita, Shin-ichiro, Masahiro Tanaka, and Masahiko Arai. "Synthesis of quinazoline-2,4(1H,3H)-dione from carbon dioxide and 2-aminobenzonitrile using mesoporous smectites incorporating alkali hydroxide." Catalysis Science & Technology 4, no. 6 (2014): 1563. http://dx.doi.org/10.1039/c3cy00977g.

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25

Shibata, Kengo, Kosaku Kato, Constantine Tsounis, Tomoki Kanazawa, Daling Lu, Shunsuke Nozawa, Akira Yamakata, Osamu Ishitani, and Kazuhiko Maeda. "Synthesis of Copolymerized Carbon Nitride Nanosheets from Urea and 2‐Aminobenzonitrile for Enhanced Visible Light CO 2 Reduction with a Ruthenium(II) Complex Catalyst." Solar RRL 4, no. 8 (December 19, 2019): 1900461. http://dx.doi.org/10.1002/solr.201900461.

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26

Majhi, Biju, and Brindaban C. Ranu. "Palladium-Catalyzed Norbornene-Mediated Tandem ortho-C–H-Amination/ipso-C–I-Cyanation of Iodoarenes: Regiospecific Synthesis of 2-Aminobenzonitrile." Organic Letters 18, no. 17 (August 23, 2016): 4162–65. http://dx.doi.org/10.1021/acs.orglett.6b02113.

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27

Hulla, Martin, Sami M. A. Chamam, Gabor Laurenczy, Shoubhik Das, and Paul J. Dyson. "Delineating the Mechanism of Ionic Liquids in the Synthesis of Quinazoline-2,4(1H ,3H )-dione from 2-Aminobenzonitrile and CO2." Angewandte Chemie 129, no. 35 (July 26, 2017): 10695–99. http://dx.doi.org/10.1002/ange.201705438.

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28

Hulla, Martin, Sami M. A. Chamam, Gabor Laurenczy, Shoubhik Das, and Paul J. Dyson. "Delineating the Mechanism of Ionic Liquids in the Synthesis of Quinazoline-2,4(1H ,3H )-dione from 2-Aminobenzonitrile and CO2." Angewandte Chemie International Edition 56, no. 35 (July 26, 2017): 10559–63. http://dx.doi.org/10.1002/anie.201705438.

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29

Chen, Jiuxi, Leping Ye, and Weike Su. "Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles." Org. Biomol. Chem. 12, no. 41 (August 22, 2014): 8204–11. http://dx.doi.org/10.1039/c4ob00978a.

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30

Jin, Yinghui, Yan Zhao, Yonggang Yang, Lirong Wang, Changyong Li, and Suotang Jia. "Two-color resonance enhanced multi-photon ionization and mass analyzed threshold ionization spectroscopy of 2-aminobenzonitrile and the CN substitution effect." Chemical Physics Letters 692 (January 2018): 395–401. http://dx.doi.org/10.1016/j.cplett.2017.12.073.

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31

Chen, Jiuxi, Leping Ye, and Weike Su. "ChemInform Abstract: Palladium-Catalyzed Direct Addition of Arylboronic Acids to 2-Aminobenzonitrile derivatives: Synthesis, Biological Evaluation and in Silico Analysis of 2-Aminobenzophenones, 7-Benzoyl-2-oxoindolines, and 7-Benzoylindoles." ChemInform 46, no. 11 (February 24, 2015): no. http://dx.doi.org/10.1002/chin.201511093.

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32

Ma, Jun, Jiayin Hu, Wenjing Lu, Zhaofu Zhang, and Buxing Han. "Theoretical study on the reaction of CO2 and 2-aminobenzonitrile to form quinazoline-2,4(1H,3H)-dione in water without any catalyst." Physical Chemistry Chemical Physics 15, no. 40 (2013): 17333. http://dx.doi.org/10.1039/c3cp52977k.

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33

Zhang, Xuan, Ziqi Wen, Hongxing Zhang, Weihua Han, Jinyi Ma, Renbo Wei, and Xiufu Hua. "Dielectric Properties of Azo Polymers: Effect of the Push-Pull Azo Chromophores." International Journal of Polymer Science 2018 (2018): 1–10. http://dx.doi.org/10.1155/2018/4541937.

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The relationship between the structure and the dielectric properties of the azo polymers was studied. Four azo polymers were synthesized through the azo-coupling reaction between the same precursor (PAZ) and diazonium salts of 4-aminobenzoic acid ethyl ester, 4-aminobenzonitrile, 4-nitroaniline, and 2-amino-5-nitrothiazole, respectively. The precursor and azo polymers were characterized by 1H NMR, FT-IR, UV-vis, GPC, and DSC. The dielectric constant and dielectric loss of the samples were measured in the frequency range of 100 Hz–200 kHz. Due to the existence of the azo chromophores, the dielectric constant of the azo polymers increases compared with that of the precursor. In addition, the dielectric constant of the azo polymers increases with the increase of the polarity of the azo chromophores. A random copolymer (PAZ-NT-PAZ) composed of the azo polymer PAZ-NT and the precursor PAZ was also prepared to investigate the content of the azo chromophores on the dielectric properties of the azo polymers. It showed that the dielectric constant increases with the increase of the azo chromophores. The results show that the dielectric constant of this kind of azo polymers can be controlled by changing the structures and contents of azo chromophores during the preparation process.

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34

Ren, Ying, Ting-Ting Meng, Jianfeng Jia, and Hai-Shun Wu. "A computational study on the chemical fixation of carbon dioxide with 2-aminobenzonitrile catalyzed by 1-butyl-3-methyl imidazolium hydroxide ionic liquids." Computational and Theoretical Chemistry 978, no. 1-3 (December 2011): 47–56. http://dx.doi.org/10.1016/j.comptc.2011.09.032.

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35

Schmies, Matthias, Alexander Patzer, Sarah Kruppe, Mitsuhiko Miyazaki, Shun‐ichi Ishiuchi, Masaaki Fujii, and Otto Dopfer. "Microsolvation of the 4‐Aminobenzonitrile Cation (ABN + ) in a Nonpolar Solvent: IR Spectra of ABN + L n (L=Ar and N 2 , n ≤4)." ChemPhysChem 14, no. 4 (December 3, 2012): 728–40. http://dx.doi.org/10.1002/cphc.201200790.

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36

Belai, Nebebech, and Samuel R. White. "Determination of Unsulfonated Aromatic Amines in FD&C Yellow No. 5 and FD&C Yellow No. 6 by Liquid Chromatography–Triple Quadrupole Mass Spectrometry." Journal of AOAC INTERNATIONAL 102, no. 2 (March 1, 2019): 580–89. http://dx.doi.org/10.5740/jaoacint.18-0165.

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Abstract Background: This paper describes a simple and sensitive ultra-HPLC–triple quadrupole MS (LC-MS/MS) method for the determination of six unsulfonated aromatic amines in the color additives FD&C Yellow No. 5 (Y5) and FD&C Yellow No. 6 (Y6). The six amines determined by thismethod are aniline (ANL), benzidine (BNZ), 4-aminobiphenyl (4ABP), 4-aminoazobenzene (4AAB), 2-aminobiphenyl (2ABP), and 4-aminobenzonitrile (4ABN). Objective: This method is intended foruse in batch certification of the color additives by the U.S. Food and Drug Administration (FDA) to ensure that each lot meets published specifications for coloring foods, drugs, and cosmetics. Methods: A modified quick, easy, cheap, effective, rugged, and safe (QuEChERS) procedure is used for extraction of the amines. Quantitative determination was performed in electrospray positive ionization and multiple-reaction monitoring modes. Results: Validation of the method demonstrated overall recovery of 101–115% and precision of 1.74–9.78% for all analytes. Excellent regression coefficients were obtained, with values >0.999. Conclusions: The validated method was successfully used for the analyses of 30 Y5 and Y6 samples and provided results that are consistent with results from the current method used by FDA, with greater sensitivity and low matrix effects. Highlights: The validation results demonstrate that the new LC-MS/MS method is applicable for use in routine batch certification.

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37

Pilon, Adhan, Ana Rita Brás, Leonor Côrte-Real, Fernando Avecilla, Paulo J. Costa, Ana Preto, M. Helena Garcia, and Andreia Valente. "A New Family of Iron(II)-Cyclopentadienyl Compounds Shows Strong Activity against Colorectal and Triple Negative Breast Cancer Cells." Molecules 25, no. 7 (March 30, 2020): 1592. http://dx.doi.org/10.3390/molecules25071592.

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A family of compounds with the general formula [Fe(η5-C5H5)(CO)(PPh3)(NCR)]+ has been synthesized (NCR = benzonitrile (1); 4-hydroxybenzonitrile (2); 4-hydroxymethylbenzonitrile (3); 4-aminobenzonitrile (4); 4-bromobenzonitrile (5); and, 4-chlorocinnamonitrile (6)). All of the compounds were obtained in good yields and were completely characterized by standard spectroscopic and analytical techniques. Compounds 1, 4, and 5 crystallize in the monoclinc P21/c space group and packing is determined by short contacts between the phosphane phenyl rings and cyclopentadienyl (compounds 1 and 4) or π-π lateral interactions between the benzonitrile molecules (complex 5). DFT and TD-DFT calculations were performed to help in the interpretation of the experimental UV-Vis. data and assign the electronic transitions. Cytotoxicity studies in MDA-MB-231 breast and SW480 colorectal cancer-derived cell lines showed IC50 values at a low micromolar range for all of the compounds in both cell lines. The determination of the selectivity index for colorectal cells (SW480 vs. NCM460, a normal colon-derived cell line) indicates that the compounds have some inherent selectivity. Further studies on the SW480 cell line demonstrated that the compounds induce cell death by apoptosis, inhibit proliferation by inhibiting the formation of colonies, and affect the actin-cytoskeleton of the cells. These results are not observed for the hydroxylated compounds 2 and 3, where an alternative mode of action might be present. Overall, the results indicate that the substituent at the nitrile-based ligand is associated to the biological activity of the compounds.

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38

Tamaddon, Fatemeh, and Farzaneh Pouramini. "Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds." Synlett 25, no. 08 (March 18, 2014): 1127–31. http://dx.doi.org/10.1055/s-0033-1340986.

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39

Roesky, Herbert W., Birgit Meller-Rehbein, and Mathias Noltemeyer. "Synthese und Reaktionen von 2-N,N-Bis(trimethylsilyl)aminobenzonitril – Kristallstrukturen von N≡C(C6H4)N = MoCl3 · 3 MeCN und [(Me3Si)2N(C6H4)CN]2TiCl4 / Synthesis and Reactions of 2-N,N-Bis(trimethylsilyl)aminobenzonitrile – Crystal Structure of N=C(C6H4)N=MoCl3 · 3 MeCN and [(Me3Si)2N(C6H4)CN]2TiCl4." Zeitschrift für Naturforschung B 46, no. 8 (August 1, 1991): 1059–64. http://dx.doi.org/10.1515/znb-1991-0815.

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The 2-(Me3Si)2N(C6H4)CN (1), reacts with NbCl5, MoCl5 and WCl6 to give the nitrogen complexes NC(C6H4)N = NbCl3 (2), NC(C6H4)N = MoCl3·3 MeCN (3) and NC(C6H4)N = WCl4 (4), and with TiCl4 to form the coordination product [(Me3Si)2N(C6H4)CN]2TiCl4 (5). The crystal structures of 3 and 5 are reported.

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40

Nale, Deepak B., Siddhesh D. Saigaonkar, and Bhalchandra M. Bhanage. "An efficient synthesis of quinazoline-2,4(1H,3H)-dione from CO2 and 2-aminobenzonitrile using [Hmim]OH/SiO2 as a base functionalized Supported Ionic Liquid Phase Catalyst." Journal of CO2 Utilization 8 (December 2014): 67–73. http://dx.doi.org/10.1016/j.jcou.2014.08.001.

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41

Tamaddon, Fatemeh, and Farzaneh Pouramini. "ChemInform Abstract: Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds." ChemInform 45, no. 44 (October 16, 2014): no. http://dx.doi.org/10.1002/chin.201444169.

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42

ROESKY, H. W., B. MELLER-REHBEIN, and M. NOLTEMEYER. "ChemInform Abstract: Synthesis and Reactions of 2-N,N-Bis(trimethylsilyl)aminobenzonitrile - Crystal Structure of NC(C6H4)N=MoCl3×3 MeCN and (( Me3Si)2N(C6H4)CN)2TiCl4." ChemInform 22, no. 46 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199146262.

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43

HOWELLS, B. D., J. MCCOMBIE, T. F. PALMER, J. P. SIMONS, and A. WALTERS. "ChemInform Abstract: Laser-Induced Fluorescence Spectroscopy and Structure of Microsolvated Molecular Clusters. Part 2. Laser-Induced Fluorescence Spectroscopy of Jet-Cooled Ethyl 4-Aminobenzoate, Methyl 4-Aminobenzoate, 4- Aminobenzonitrile and Their Dim." ChemInform 24, no. 1 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199301041.

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44

Roy, Bivas Chandra, Sk Abdus Samim, Dibyajyoti Panja, and Sabuj Kundu. "Tandem synthesis of quinazolinone scaffolds from 2-aminobenzonitriles using aliphatic alcohol–water system." Catalysis Science & Technology 9, no. 21 (2019): 6002–6. http://dx.doi.org/10.1039/c9cy01094g.

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45

Kumar, Subodh, Sanny Verma, Efrat Shawat, Gilbert Daniel Nessim, and Suman L. Jain. "Amino-functionalized carbon nanofibres as an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2and 2-aminobenzonitriles." RSC Advances 5, no. 31 (2015): 24670–74. http://dx.doi.org/10.1039/c5ra01900a.

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46

Howells, Brendan D., June McCombie, T. Frank Palmer, John P. Simons, and Alan Walters. "Laser-induced fluorescence spectroscopy and structure of microsolvated molecular clusters. Part 2.—Laser-induced fluorescence spectroscopy of jet-cooled ethyl 4-aminobenzoate, methyl 4-aminobenzoate, 4-aminobenzonitrile and their dimethylamino and pyrrolidino derivatives." J. Chem. Soc., Faraday Trans. 88, no. 18 (1992): 2595–601. http://dx.doi.org/10.1039/ft9928802595.

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47

Chen, Shangqing, Zheng Wang, Jiayin Hu, Yafei Guo, and Tianlong Deng. "Efficient transformation of CO2 into quinazoline-2,4(1H,3H)-diones at room temperature catalyzed by a ZnI2/NEt3 system." New Journal of Chemistry 43, no. 41 (2019): 16164–68. http://dx.doi.org/10.1039/c9nj04302k.

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The readily available ZnI₂/NEt₃ system promotes the efficient transformation of CO₂ and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones at room temperature and low CO₂ pressure.

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48

Geng, Xiao, Xia Wu, Can Wang, Peng Zhao, You Zhou, Xuan Sun, Ling-Jiao Wang, Wen-Juan Guan, Yan-Dong Wu, and An-Xin Wu. "NaHS·nH2O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles." Chemical Communications 54, no. 90 (2018): 12730–33. http://dx.doi.org/10.1039/c8cc07599a.

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An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH₂O is used as a novel umpolung reagent for the first time in organic synthesis.

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Zhao, Ya-Nan, Bing Yu, Zhen-Zhen Yang, and Liang-Nian He. "Magnetic base catalysts for the chemical fixation of carbon dioxide to quinazoline-2,4(1H,3H)-diones." RSC Adv. 4, no. 55 (2014): 28941–46. http://dx.doi.org/10.1039/c4ra03659j.

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TBD-functionalized Fe₃O₄ was proven to be an efficient and recyclable magnetic heterogeneous catalyst for the chemical fixation of CO₂ with 2-aminobenzonitriles under mild conditions.

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50

Nale, Deepak B., Surjyakanta Rana, Kulamani Parida, and Bhalchandra M. Bhanage. "Amine functionalized MCM-41: an efficient heterogeneous recyclable catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from carbon dioxide and 2-aminobenzonitriles in water." Catal. Sci. Technol. 4, no. 6 (2014): 1608–14. http://dx.doi.org/10.1039/c3cy00992k.

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Covalently linked amine functionalized MCM-41 was investigated as an efficient catalyst for the synthesis of various quinazoline-2,4(1H,3H)-dione derivatives from 2-aminobenzonitriles and carbon dioxide in water.

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