Ярославль, Ярославская область, Россия
Ярославль, Ярославская область, Россия
A method for the synthesis of ortho-dicarbonitriles containing heterocyclic systems of indazole, quinoline, benzothiazole, and tetrahydroquinoline not described in the literature has been developed based on the reaction of 4-bromo-5-nitrophthalonitrile and primary heterylamines.
nucleophilic substitution, substituted ortho-dicarbonitriles, indazole, quinoline, benzothiazole, tetrahydroquinoline, 4-bromo-5-nitrophthalonitril
1. Terrier F. Nucleophilic aromatic displacement: the influence of the nitro group, VSH Publishers, New York, 1991.
2. Abramov I.G., Dorogov M.V., Smirnov A.V., Ivanovskii S.A., Abramova M.B., Plachtinsky V.V. The differing reactivity of the bromo and nitro groups in 4-bromo-5-nitrophthalonitrile towards nucleophilic attack. Mendeleev Commun. 2000. V. 2. P. 78. DOIhttps://doi.org/10.1070/MC2000v010n02ABEH001147.
3. Chirkova Z.V., Filimonov S.I., Abramov I.G. Synthesis of Functional Derivatives of Benzofuran-5,6-dicarboxylic Acids. Russian Journal of General Chemistry. 2019. V. 89. Issue 6. P. 1307-1309. DOI: 10.1134/ S1070363219060276/
4. Filimonov S.I., Chirkova Zh.V., Abramov I.G., Firgang S.I., Stashina G.A., Suponitsky K.Yu. Synthesis of Novel Substituted 4-Hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6,7-dicarbonitriles. Heterocycles. 2011. V. 83, N 4. P. 755-763. DOI:https://doi.org/10.3987/COM-10-12128.
5. Abramov I.G., Smirnov A.V., Kalandadze L.S, Plakhtinskii V.V., Sakharov V.N. Synthesis of Substituted Dibenzoxazepine Using of 4-Bromo-5-nitrophthalonitrile. Heterocycles. 2003. V. 60. N 7. P. 1611-1614. DOI:https://doi.org/10.3987/COM-03-9739/
6. Tikhomirova T.V., Gruzdeva O.M., Galanin N.E., Shaposhnikov G.P., Abramov I.G. Phthalocyanines containing macrocyclic and azo chromophores in the molecule. Russian Journal of General Chemistry. 2016. V. 86. Issue 4. P. 848-853. DOIhttps://doi.org/10.1134/S1070363216040150.
7. Berezin D.B., Kustov A.V., Krestyaninov M.A., Batov D.V., Kukushkina N.V., Shukhto O.V. The behavior of monocationic chlorin in water and aqueous solutions of non-ionic surfactant Tween 80 and potassium iodide. J. Molec. Liquids. 2019. V. 283. P. 532-536. DOI:https://doi.org/10.1016/j.molliq.2019.03.091
8. Mikhailova A.I., Znoiko S.A., Maizlish V.E., Shaposhnikov G.P, Abramov l.G., Abramova M.B. Nucleophilic Substitution of 4-Bromo-5-nitrophthalodinitrile: XVII. Synthesis and Properties of Bifunctionally Substituted Metal Phthalocyanines with Aryloxy and Nitro Groups. Russian Journal of General Chemistry. 2018. V. 88. Issue 7. P. 1425-1429. DOI:https://doi.org/10.1134/S1070363218040205.
9. Znoyko S.A., Savinova A.I., Maizlish V.E., Shaposhnikov G.P., Abramov I.G. Nucleophilic substitution of 4-bromo-5-nitrophthalodinitrile: XIII. Synthesis and properties of 4-(1-benzotriazolyl)-5-(4-tritylphenoxy)phthalonitrile and phthalocyanines based thereon. Russian Journal of General Chemistry. 2016. V. 86. Issue 6. P. 1345-1352. DOI:https://doi.org/10.1134/S1070363216060207.
10. Chirkova Z.V., Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Hitge R., Petzer J.P., Suponitsky K.Y. Optimization of pyrrolo[3,4-f]indole-5,7-dione and indole-5,6-dicarbonitrile derivatives as inhibitors of monoamine oxidase. Drug Development Research. 2019. V. 80. Issue 7. P. 970-980. DOI:https://doi.org/10.1002/ddr.21576.
11. Chirkova Zh.V, Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Petzer J.P., Suponitsky K.Yu. An evaluation of synthetic indole derivatives as inhibitors of monoamine oxidas. Bioorganic and Medicinal Chemistry Letters. 2016. V. 26 (9). P. 2214-2219. DOI:https://doi.org/10.1016/j.bmcl.2016.03.060.
12. Berezin D.B., Makarov V.V., Znoyko V.E., Mayzlish S.A., Kustov A.V. Aggregation water soluble octaanionicph thalocyanines behavior and their photoinactivation antimicrobial effect in vitro. Mend. Commun, 2020. V. 30. N 5. P. 621-623. DOI:https://doi.org/10.1016/j.mencom.2020.09.023.
13. Caterino M., D'Aria F., Kustov A.V., Belykh D.V., Khudyaeva I.S., Starseva O.M., Berezin D.B., Pylina Y.I., Usacheva T.R., Amato J., Giancola C. Selective binding of a bioactive porphyrin-based photosensitizer to the G-quadruplex from the KRAS oncogene promoter. Intern. J. Biol. Macromolecules. 2020. V. 145. P. 244-251. DOI:https://doi.org/10.1016/j.ijbiomac.2019.12.152.
14. Filimonov S.I., Chirkova Zh.V., Abramov I.G., Firgang S.I., Stashina G.A., Suponitsky K.Yu. Synthesis of 2-oxo- and 2-thioxo-5-(benzofuran-2-yl)-tetrahydropyrimidines. Mendeleev Commun. 2011. V. 21. N 6. P. 332-333. DOI:https://doi.org/10.1016/j.mencom.2011.01.019.
15. Chirkova Zh.V., Filimonov S.I., Abramov I.G., Firgang S.I., Stashina G.A., Strelenko Yuri A., Khakimov D.V., Pivina T.S., Samet A.V., Suponitsky K.Yu. Base-induced transformations of ortho-nitrobenzylketones: intramolecular displacement of nitro group versus nitro-nitrite rearrangement. Tetrahedron. 2012. N 30. V. 68 P. 5991–5997. DOI:https://doi.org/10.1016/j.tet.2012.05.034
16. Chirkova Zh.V., Kabanova M.V., Sharunov V.S., Danilova A.S., Abramov I.G., Filimonov S.I., Luferenko D.V., Soloviev M.E. New Nitrogen-Containing Five-Membered Heterocyclic ortho - Dicarbonitriles for Preparation of Macroheterocycles. Macroheterocycles. 2014. Vol. 7 (3), P. 296-301. DOI:https://doi.org/10.6060/mhcl40378c.
17. Abramov I.G., Smirnov A.V., Ivanovskii S.A., Abramova M.B., Plachtinsky V.V., Belysheva M.S. Synthesis of oxygen-containing heterocyclic ortho-dinitriles based on 4-bromo-5-nitrophthalonitrile. Mendeleev Commun. 2001. N 2. P.80-81. DOI:https://doi.org/10.1070/MC2001v011n02ABEH001400.
