МЕТОДЫ СИНТЕЗА НИТРОПИРИДИНОВ
Ключевые слова:
производные пиридина, синтез нитропиридинов, нитрование производных пиридина
Аннотация
Обоснование. Производные пиридина широко применяются в фармацевтике, агрохимии, а также в производстве новых материалов. Пиридиновое и пиперидиновое кольца являются основными структурными фрагментами многочисленных природных алкалоидов, обладающих широким спектром биологической активности. Многие из этих алкалоидов проявляют противораковую активность, а также действие, направленное на лечение неврологических расстройств и других заболеваний, и продолжают быть ценными объектами исследований, стимулирующими открытие новых лекарств. Высокоэффективные методы синтеза различных производных пиридинов и энантиомеров пиперидинов будут продолжать пользоваться высоким спросом. В связи с этим анализ и систематизация основных результатов исследований по синтезу нитропиридинов является актуальной задачей.
Цель. Обобщить и систематизировать основные методы синтеза нитропроизводных пиридина с начала прошлого века и до настоящего времени.
Материалы и методы. Для достижения поставленной цели исследования был произведён обзор научной литературы по основным методам получения нитропиридинов.
Результаты. В данном литературном обзоре представлены результаты экспериментальных исследований по синтезу нитропроизводных пиридина, начиная с первой половины XX в. и до настоящего времени.
Заключение. Таким образом, удалось обобщить накопленный к настоящему дню разрозненный, но достаточно обширный фактический материал, посвященный получению нитропроизводных пиридина. Рассмотрены несколько основных подходов к синтезу, исходя из алифатических соединений, путем нитрования пиридина и его производных, а также окислением аминопиридинов.
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Литература
1. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Gil’manova T.B., Petrov E.S. Izucheniye nitrovaniya 3-gidroksipiridinov [Study of nitration of 3-hydroxypyridines]. Vestnik KTU, 2013, pp. 32-33.
2. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Sobachkina T.N., Petrov E.S. Povedeniye 3-aminoproizvodnykh piridina v reaktsii nitrovaniya [Behavior of 3-amino derivatives of pyridine in the nitration reaction]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2012, pp. 41-43.
3. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Nikitin V.G., Petrov E.S., Nikolayev E.A. Osobennosti nitrovaniya N-okisey piridina [Features of nitration of N-oxides of pyridine]. Vestnik KTU, 2014, pp. 19-20.
4. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Sobachkina T.N., Nikolayev E.A. Povedeniye metoksiproizvodnykh N-okisi piridina v reaktsii nitrovaniya [Behavior of methoxy derivatives of N-oxide of pyridine in the nitration reaction]. Vestnik KTU, 2014, vol. 17, issue 13, pp. 80-82.
5. Falyakhov I.F., Gil’manov R.Z., Khayrutdinov F.G., Bol’shakova T.G., Akhtyamova Z.G., Nikitin V.G. Zakonomernosti nitrovaniya gidroksiproizvodnykh piridina [Regularities of nitration of pyridine hydroxy derivatives]. Vestnik KTU, 2010, pp. 613-616.
6. Falyakhov I.F., Gil’manov R.Z., Khayrutdinov F.G., Sharnin G.P., Akhtyamova Z.G. Zakonomernosti nitrovaniya piridina i yego alkilproizvodnykh [Regularities of nitration of pyridine and its alkyl derivatives]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2010, pp. 606-608.
7. Falyakhov I.F., Gil’manov R.Z., Sharnin G.P., Khayrutdinov F.G., Sobachkina T.N., Nikitin V.G. Zakonomernosti nitrovaniya aminoproizvodnykh piridina [Regularities of nitration of amine derivatives of pyridine]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2010, pp. 621-623.
8. Angela R. Sherman, Ramiah Muruganю C–N Bond Making Reactions at a Pyridine Ring. Advances in Heterocyclic Chemistry, 2015, vol. 114, pp. 227-269. https://doi.org/10.1016/bs.aihch.2015.03.001
9. Bakke J.M. Nitropyridines, their synthesis and reactions. J. Heterocycl. Chem., 2005, vol. 42, pp. 463-474. https://doi.org/10.1002/JHET.5570420313
10. Baumgarten H.E., SuH. C.-F., KriegerA.L. Dechlorination of Some Chloronitropicolines. J. Am. Chem. Soc., 1954, vol. 76 (2), pp. 596–599. https://doi.org/10.1021/JA01631A080
11. Bernstein J., Stearns B., Shaw E., Lott W.A. II. Derivatives of 2,6-Diaminopyridine1. J. Am. Chem. Soc., 1947, vol. 69, pp. 1151–1158. https://doi.org/10.1021/JA01197A048
12. David O’Hagan. Pyrrole, pyrrolidine pyridine, piperidine, azepine and tropane alkaloids. Natural Product Reports, 2000, vol. 17(5), pp. 435-46. https://doi.org/10.1039/a707613d
13. De Selms R.C. Unprecedented orientation in the nitration of certain 3-pyridinols. J. Org. Chem., 1968, vol. 33, pp. 478-480.
14. Den Hertog H.J., Combe W.P. Reactivity of 4-nitropyridine-N-oxide: Preparation of 4-substituted derivatives of pyridine-N-oxide and pyridine. Rec. trav. chim., 1951, vol. 70, pp 581-590. https://doi.org/10.1002/RECL.19510700704
15. Den Hertog H.J., Overhoff J. Über die Nitrierung des Pyridins. (Darstellung des 2-Nitropyridins). Rec. trav. chim., 1930, vol. 49, pp. 552-556.
16. Den Hertog H.J., van Weeren J.W. Nitration of 3,5-diethoxypyridine. Rec. trav. chim., 1948, vol. 67, pp. 980-982. https://doi.org/10.1002/RECL.19480671207
17. Francisco Sánchez-Viesca, Martha Berros;Ma. Reina Gómez. Electric hindrance and other factors in 2-aminopyridine nitration. TIP Revista Especializada en Ciencias Químico-Biológicas, 2013, vol. 16(1), pp. 36-41.
18. Hamana M., Yoshimura H. Decomposition of 4-Nitropyridine. J. Pharm. Soc. Japan., 1952, vol. 72, pp. 1051-1054. https://doi.org/10.1248/YAKUSHI1947.72.8_1051
19. Ivanova E.V., Nikishina M.B., Mukhtorov L.G., Perelomov L.V., Atroshchenko Yu.M. Investigation of the fungicidal activity of new derivatives of 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1]nonan-2-one. Siberian Journal of Life Sciences and Agriculture, 2021, vol. 13, no. 5, pp. 307-320. https://doi.org/10.12731/2658-6649-2021-13-5-307-320
20. José Sebastião Santos Neto, GilsonZen. Ten years of progress in the synthesis of six-membered N-heterocycles from alkynes and nitrogen sources. Tetrahedron, 2020, vol. 76, no. 4, pp. 130876. https://doi.org/10.1016/j.tet.2019.130876
21. Katritzky A.R., Scriven E.F.V., Majumder S., Akhmedova R.G., Vakulenko A.V., Akhmedov N.G., Murugan R., Abboud K.A. Preparation of nitropyridines by nitration of pyridines with nitric acid. Org. Biomol. Chem., 2005, vol. 3, pp. 538-541. https://doi.org/10.1039/B413285H
22. Kirpal A., Reiter E. 3-Nitropyridin und seine Derivate. Ber., 1925, vol. 58, pp. 699-701.
23. Koenigs E., Gerdes H. C., Sirot A. Über die Nitrierung des 3-Äthoxy-pyridins. Ber., 1928, vol. 61, pp. 1022-1030.
24. Koenigs E., Mields M., Gurlt H. Nitrierungsprodukte des γ-Amino-pyridins. Ber., 1924, vol. 57, pp. 1179–1187. https://doi.org/10.1002/CBER.19240570725
25. Kroehnke F., Schaefer H. Die Darstellung des 4-Nitro-pyridins und seine Molekülverbin-dungen mit Phenolen. Chem. Ber., 1962, vol. 95, pp. 1098-1103. https://doi.org/10.1002/CBER.19620950506
26. Ling Y, Hao ZY, Liang D, Zhang CL, Liu YF, Wang Y. The expanding role of pyridine and dihydropyridine scaffolds in drug design. Drug Design, Development and Therapy, 2021, vol. 15, pp 4289-4338. https://doi.org/10.2147/DDDT.S329547
27. Manfred Schlosser. Reactions of Pyridines, Benzopyridines, and Azapyridines with Organomagnesiums and Organolithiums. Metalation of Azines and Diazines, 2013, pp. 171-222. https://doi.org/10.1007/7081_2012_96
28. Pat. DE 568,549. Verfahren zur Darstellung von 2-Alkoxy-5-nitropyridinen / Dr Erich H. заявл. 12.01.1932; опубл. 21.01.1933.
29. Pennington L.D., Moustakas D.T. The necessary nitrogen atom: A versatile high-impact design element for multiparameter optimization. J Med Chem., 2017, vol. 60 (9), pp. 3552–3579. https://doi.org/10.1021/acs.jmedchem.6b01807
30. Prudel C., Huwig K., Kazmaier U. Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines. Chem. Eur. J., 2020, vol. 26, pp. 3181–3188. https://doi.org/10.1002/chem.202000051
31. Renat H. Mizzoni. Nitropyridines and Reduction Products (Except Amines). 2008, pp.1-40. https://doi.org/10.1002/9780470186725.ch1
32. Sagitullina G.P., Garkushenko A.K., Silina E.O., Sagitullin R.S. Nitropyridines. 7*. Synthesis of nitropyridines from nitro-malonic dialdehyde. Chemistry of Heterocyclic Compounds, 2009, vol. 45 (8), pp. 948-951. https://doi.org/10.1007/S10593-009-0366-8
33. Suzuki H., Iwaya M., Mori T. C-Nitration of pyridine by the kyodai-nitration modified by the Bakke procedure. A simple route to 3-nitropyridine and mechanistic aspect of its formation. Tetrahedron Lett., 1997, vol. 38, pp. 5647-5650. https://doi.org/10.1016/S0040-4039%2897%2901229-X
34. Takahashi T., Yamamoto Y. Syntheses of Heterocyclic Compounds of Nitrogen. J. Pharm. Soc. Japan., 1949, vol. 69, pp. 408.
35. Tohru Takei, Takumi Ohki, Yosuke Harada, et al. Preparation of dibromopyridines having –(CH2)m–SO3Na groups as monomers for new polypyridines. Tetrahedron Letters, 2012, vol. 53, pp. 5907. https://doi.org/10.1016/J.TETLET.2012.08.086
36. 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. J Med Chem., 2014, vol. 57(24), pp. 10257–10274. https://doi.org/10.1021/jm501100b
37. Von Schichk O.V., Binz A., Schulz A. Derivate des 3-Amino-pyridins. Ber., 1936, vol. 69, pp. 2593-2605. https://doi.org/10.1002/CBER.19360691202
38. Weidel H., Murmann E. Zur Kenntniss einiger Nitroverbindungen der Pyridinreihe. Monatshefte für Chemie, 1895, vol. 16, pp. 749-759. https://doi.org/10.1007/BF01519024
2. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Sobachkina T.N., Petrov E.S. Povedeniye 3-aminoproizvodnykh piridina v reaktsii nitrovaniya [Behavior of 3-amino derivatives of pyridine in the nitration reaction]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2012, pp. 41-43.
3. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Nikitin V.G., Petrov E.S., Nikolayev E.A. Osobennosti nitrovaniya N-okisey piridina [Features of nitration of N-oxides of pyridine]. Vestnik KTU, 2014, pp. 19-20.
4. Gil’manov R.Z., Falyakhov I.F., Khayrutdinov F.G., Sobachkina T.N., Nikolayev E.A. Povedeniye metoksiproizvodnykh N-okisi piridina v reaktsii nitrovaniya [Behavior of methoxy derivatives of N-oxide of pyridine in the nitration reaction]. Vestnik KTU, 2014, vol. 17, issue 13, pp. 80-82.
5. Falyakhov I.F., Gil’manov R.Z., Khayrutdinov F.G., Bol’shakova T.G., Akhtyamova Z.G., Nikitin V.G. Zakonomernosti nitrovaniya gidroksiproizvodnykh piridina [Regularities of nitration of pyridine hydroxy derivatives]. Vestnik KTU, 2010, pp. 613-616.
6. Falyakhov I.F., Gil’manov R.Z., Khayrutdinov F.G., Sharnin G.P., Akhtyamova Z.G. Zakonomernosti nitrovaniya piridina i yego alkilproizvodnykh [Regularities of nitration of pyridine and its alkyl derivatives]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2010, pp. 606-608.
7. Falyakhov I.F., Gil’manov R.Z., Sharnin G.P., Khayrutdinov F.G., Sobachkina T.N., Nikitin V.G. Zakonomernosti nitrovaniya aminoproizvodnykh piridina [Regularities of nitration of amine derivatives of pyridine]. Vestnik Kazanskogo tekhnologicheskogo universiteta, 2010, pp. 621-623.
8. Angela R. Sherman, Ramiah Muruganю C–N Bond Making Reactions at a Pyridine Ring. Advances in Heterocyclic Chemistry, 2015, vol. 114, pp. 227-269. https://doi.org/10.1016/bs.aihch.2015.03.001
9. Bakke J.M. Nitropyridines, their synthesis and reactions. J. Heterocycl. Chem., 2005, vol. 42, pp. 463-474. https://doi.org/10.1002/JHET.5570420313
10. Baumgarten H.E., SuH. C.-F., KriegerA.L. Dechlorination of Some Chloronitropicolines. J. Am. Chem. Soc., 1954, vol. 76 (2), pp. 596–599. https://doi.org/10.1021/JA01631A080
11. Bernstein J., Stearns B., Shaw E., Lott W.A. II. Derivatives of 2,6-Diaminopyridine1. J. Am. Chem. Soc., 1947, vol. 69, pp. 1151–1158. https://doi.org/10.1021/JA01197A048
12. David O’Hagan. Pyrrole, pyrrolidine pyridine, piperidine, azepine and tropane alkaloids. Natural Product Reports, 2000, vol. 17(5), pp. 435-46. https://doi.org/10.1039/a707613d
13. De Selms R.C. Unprecedented orientation in the nitration of certain 3-pyridinols. J. Org. Chem., 1968, vol. 33, pp. 478-480.
14. Den Hertog H.J., Combe W.P. Reactivity of 4-nitropyridine-N-oxide: Preparation of 4-substituted derivatives of pyridine-N-oxide and pyridine. Rec. trav. chim., 1951, vol. 70, pp 581-590. https://doi.org/10.1002/RECL.19510700704
15. Den Hertog H.J., Overhoff J. Über die Nitrierung des Pyridins. (Darstellung des 2-Nitropyridins). Rec. trav. chim., 1930, vol. 49, pp. 552-556.
16. Den Hertog H.J., van Weeren J.W. Nitration of 3,5-diethoxypyridine. Rec. trav. chim., 1948, vol. 67, pp. 980-982. https://doi.org/10.1002/RECL.19480671207
17. Francisco Sánchez-Viesca, Martha Berros;Ma. Reina Gómez. Electric hindrance and other factors in 2-aminopyridine nitration. TIP Revista Especializada en Ciencias Químico-Biológicas, 2013, vol. 16(1), pp. 36-41.
18. Hamana M., Yoshimura H. Decomposition of 4-Nitropyridine. J. Pharm. Soc. Japan., 1952, vol. 72, pp. 1051-1054. https://doi.org/10.1248/YAKUSHI1947.72.8_1051
19. Ivanova E.V., Nikishina M.B., Mukhtorov L.G., Perelomov L.V., Atroshchenko Yu.M. Investigation of the fungicidal activity of new derivatives of 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1]nonan-2-one. Siberian Journal of Life Sciences and Agriculture, 2021, vol. 13, no. 5, pp. 307-320. https://doi.org/10.12731/2658-6649-2021-13-5-307-320
20. José Sebastião Santos Neto, GilsonZen. Ten years of progress in the synthesis of six-membered N-heterocycles from alkynes and nitrogen sources. Tetrahedron, 2020, vol. 76, no. 4, pp. 130876. https://doi.org/10.1016/j.tet.2019.130876
21. Katritzky A.R., Scriven E.F.V., Majumder S., Akhmedova R.G., Vakulenko A.V., Akhmedov N.G., Murugan R., Abboud K.A. Preparation of nitropyridines by nitration of pyridines with nitric acid. Org. Biomol. Chem., 2005, vol. 3, pp. 538-541. https://doi.org/10.1039/B413285H
22. Kirpal A., Reiter E. 3-Nitropyridin und seine Derivate. Ber., 1925, vol. 58, pp. 699-701.
23. Koenigs E., Gerdes H. C., Sirot A. Über die Nitrierung des 3-Äthoxy-pyridins. Ber., 1928, vol. 61, pp. 1022-1030.
24. Koenigs E., Mields M., Gurlt H. Nitrierungsprodukte des γ-Amino-pyridins. Ber., 1924, vol. 57, pp. 1179–1187. https://doi.org/10.1002/CBER.19240570725
25. Kroehnke F., Schaefer H. Die Darstellung des 4-Nitro-pyridins und seine Molekülverbin-dungen mit Phenolen. Chem. Ber., 1962, vol. 95, pp. 1098-1103. https://doi.org/10.1002/CBER.19620950506
26. Ling Y, Hao ZY, Liang D, Zhang CL, Liu YF, Wang Y. The expanding role of pyridine and dihydropyridine scaffolds in drug design. Drug Design, Development and Therapy, 2021, vol. 15, pp 4289-4338. https://doi.org/10.2147/DDDT.S329547
27. Manfred Schlosser. Reactions of Pyridines, Benzopyridines, and Azapyridines with Organomagnesiums and Organolithiums. Metalation of Azines and Diazines, 2013, pp. 171-222. https://doi.org/10.1007/7081_2012_96
28. Pat. DE 568,549. Verfahren zur Darstellung von 2-Alkoxy-5-nitropyridinen / Dr Erich H. заявл. 12.01.1932; опубл. 21.01.1933.
29. Pennington L.D., Moustakas D.T. The necessary nitrogen atom: A versatile high-impact design element for multiparameter optimization. J Med Chem., 2017, vol. 60 (9), pp. 3552–3579. https://doi.org/10.1021/acs.jmedchem.6b01807
30. Prudel C., Huwig K., Kazmaier U. Stereoselective Allylic Alkylations of Amino Ketones and Their Application in the Synthesis of Highly Functionalized Piperidines. Chem. Eur. J., 2020, vol. 26, pp. 3181–3188. https://doi.org/10.1002/chem.202000051
31. Renat H. Mizzoni. Nitropyridines and Reduction Products (Except Amines). 2008, pp.1-40. https://doi.org/10.1002/9780470186725.ch1
32. Sagitullina G.P., Garkushenko A.K., Silina E.O., Sagitullin R.S. Nitropyridines. 7*. Synthesis of nitropyridines from nitro-malonic dialdehyde. Chemistry of Heterocyclic Compounds, 2009, vol. 45 (8), pp. 948-951. https://doi.org/10.1007/S10593-009-0366-8
33. Suzuki H., Iwaya M., Mori T. C-Nitration of pyridine by the kyodai-nitration modified by the Bakke procedure. A simple route to 3-nitropyridine and mechanistic aspect of its formation. Tetrahedron Lett., 1997, vol. 38, pp. 5647-5650. https://doi.org/10.1016/S0040-4039%2897%2901229-X
34. Takahashi T., Yamamoto Y. Syntheses of Heterocyclic Compounds of Nitrogen. J. Pharm. Soc. Japan., 1949, vol. 69, pp. 408.
35. Tohru Takei, Takumi Ohki, Yosuke Harada, et al. Preparation of dibromopyridines having –(CH2)m–SO3Na groups as monomers for new polypyridines. Tetrahedron Letters, 2012, vol. 53, pp. 5907. https://doi.org/10.1016/J.TETLET.2012.08.086
36. 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. J Med Chem., 2014, vol. 57(24), pp. 10257–10274. https://doi.org/10.1021/jm501100b
37. Von Schichk O.V., Binz A., Schulz A. Derivate des 3-Amino-pyridins. Ber., 1936, vol. 69, pp. 2593-2605. https://doi.org/10.1002/CBER.19360691202
38. Weidel H., Murmann E. Zur Kenntniss einiger Nitroverbindungen der Pyridinreihe. Monatshefte für Chemie, 1895, vol. 16, pp. 749-759. https://doi.org/10.1007/BF01519024
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Опубликован
2021-12-30
Как цитировать
Ivanova, E., Nikishina, M., Mukhtorov, L., Shahkeldyan, I., & Atroshchenko, Y. (2021). МЕТОДЫ СИНТЕЗА НИТРОПИРИДИНОВ. Siberian Journal of Life Sciences and Agriculture, 13(6), 177-200. https://doi.org/10.12731/2658-6649-2021-13-6-177-200
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Copyright (c) 2022 Evgeniya V. Ivanova, Maria B. Nikishina, Loik G. Mukhtorov, Irina V. Shahkeldyan, Yuri M. Atroshchenko
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