CHEMICAL PROPERTIES AND APPLICATIONS OF NITROPYRIDINES
Abstract
Background. Pyridines are one of the most common heterocycles, the derivatives of which are widely used in pharmaceuticals, agrochemistry, and also in the production of new materials. Therefore, a comprehensive study of the chemical behavior of various pyridine derivatives will continue to be an urgent task of organic chemistry. This literature review is devoted to the systematization and analysis of the chemical properties of pyridine nitro derivatives, starting from the first half of the 20th century and up to the present. The paper considers both reactions proceeding through the nitro group (reduction under the action of various chemical agents, substitution, condensation) and reactions through the pyridine cycle. The main areas of application of nitropyridines are also shown.
Purpose. Generalize and systematize the main types of reactions characteristic of nitropyridines, show the features of their chemical properties associated with the transformation of the nitro group, its effect on the mobility of substituents in the pyridine ring, as well as on the activity of the heterocycle as a whole.
Materials and methods. To achieve the goal of the study, a review of the scientific literature was made on the main types of chemical reactions characteristic of pyridine nitro derivatives and the most significant areas of their application.
Results. This paper summarizes the results of experimental studies on the chemical properties and application of nitropyridines from the beginning of the last century to the present.
Conclusion. Thus, as a result of the analysis of sources devoted to the chemical properties and application of nitropyridines, a brief literature review was compiled, including the main types of reactions characteristic of the compounds under study, and their main areas of application were identified.
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Список литературы
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da Silva J. P. et al. Electrochemical, mechanistic, and DFT studies of amine derived diphosphines containing Ru (II)cymene complexes with potent in vitro cytotoxic activity against HeLa and triple-negative breast cancer cells MDA-MB-231. Dalton Transactions. 2020. V. 49. No. 45. P. 16498-16514.
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Kamanina N. V. Optical investigations of a C70-doped 2-cyclooctylamino-5-nitropyridine–liquid crystal system. Journal of Optics A: Pure and Applied Optics. 2002. V. 4. No. 5. P. 571.
Katada I. Polarization of aromatic heterocyclic compounds. LIII. Deoxidation of pyridine and quinoline 1-oxides by thermal decomposition. J. Pharm. Soc. Japan. 1947. V. 67. P. 53-55.
Kodimuthali A. et al. A simple synthesis of aminopyridines: Use of amides as amine source. Journal of the Brazilian Chemical Society. 2010. V. 21. P. 1439-1445.
Komor R. et al. Application of different alpha-1-thioglycosides preparation methods in synthesis of 5-nitro-2-pyridyl 1-thioglycosides substrates in synthesis of conjugates with uridine moiety. Part I. Acta Poloniae Pharmaceutica. 2012. V. 69. No. 6. P. 1259-1269.
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Kumar N., Singh G., Khatoon S., Yadav A.K. Synthesis and antimicrobial activities of novel 10H-pyrido[3,2-b][1,4]benzo[b]thiazine ribofuranosides. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry. 2003. V. 42. P. 2015-2018.
Lach F., Koza P. Practical Way to Imidazo [4, 5-b] and [4, 5-c] Pyridine-2-ones via Cascade Ureidation/Palladium-Catalyzed Cyclization. ACS Combinatorial Science. 2012. V. 14. No. 9. P. 491-495.
Ling C.G., Lu S. Synthesis of new unsymmetric N,N′-dipyridylurea derivatives by selenium and selenium dioxide-catalyzed reductive carbonylation of substituted nitropyridines. Tetrahedron. 2003. V. 59. P. 8251-8256.
Murugan R. Pyridines: from lab to production. Chapter 4 - Substituent Modifications. Best Synthetic Methods. 2013. P. 375-411.
Fadli A. Pat. WO2011/69898 A1. Novel cationic aminopyridines, dye composition comprising a cationic aminopyridine, processes therefor and uses thereof / application. 03.12.2010; publ. 16.06.2011.
Sobhani-Nasab A. et al. Five-component domino synthesis of tetrahydropyridines using hexagonal PbCr x Fe12− x O19 as efficient magnetic nanocatalyst. Research on Chemical Intermediates. 2017. V. 43. No. 11. P. 6155-6165.
Tjosås F., Pettersen N.M., Fiksdahl A. α-(3-Pyridyl)malonates: preparation and synthetic applications. Tetrahedron. 2007. V. 63. P. 11893-11901.
Türker L., Variş S. A review of polycyclic aromatic energetic materials. Polycyclic Aromatic Compounds. 2009. V. 29. No. 4. P. 228-266.
Varvaresou A., Iakovou K. Derivatives of 5-Oxy-pyrido[2,3-b]quinoxaline-9-carboxylic Acid: A Tricyclic System Useful for the Synthesis of Potential Intercalators. J. Heterocyclic Chem. 2002. V. 39. P. 1173.
Vitaku E., Smith D. T., Njardarson J. T. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among US FDA approved pharmaceuticals: miniperspective. Journal of medicinal chemistry. 2014. V. 57. No. 24. P. 10257-10274.
Winkler M., Cakir B., Sander W. 3, 5-Pyridyne A Heterocyclic meta-Benzyne Derivative. Journal of the American Chemical Society. 2004. V. 126. No. 19. P. 6135-6149.
Zhang L. Y. et al. Synthetic optimization of TACOT-derived nitrogen-rich energetic compounds and reaction mechanism research. Synthetic Communications. 2021. V. 51. No. 18. P. 2808-2816.
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