Abstract
In the course of electrochemical generation the intermediate reaction products (free radicals of the nitro-and nitrosophenyl type, which appear on the cyclic voltammetric curves) were identified by ESR. The N-substituted derivatives are characterized by reduction of the dihydropyridine ring. The 4-nitrophenyl derivatives are characterized by the absence of intramolecular electron transfer during electrochemical reduction. In the case of the corresponding derivatives of 1,2-dihydropyridine intramolecular transfer of electrons and protons is possible under these conditions. Combined schemes of the primary and secondary chemical reactions involved in the electrochemical reduction of the investigated compounds are presented. It was established that the substances investigated with reference to the mechanism of the electrochemical transformations include the antihypertensive nifedipine (corinfar, fenigidine).
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References
Ya. P. Stradyn', Yu. I. Beilis, Ya. R. Uldrikis, G. Ya. Dubur, A. É. Sausin', and B. S. Chekavichus, Khim. Geterotsikl. Soedin., No. 11, 1525, 1530 (1975).
V. Skala, J. Volke, V. Ohanka, and J. Kuthan, Coll. Czech. Chem. Commun.,42, 292 (1977).
J. Ludvik, J. Klima, J. Volke, A. Kurfürst, and J. Kuthan, J. Electroanal. Chem.,138, 131 (1982).
Ya. V. Ogle, Ya. P. Stradyn', G. Ya. Dubur, V. K. Lusis, and V. P. Kadysh, Khim. Geterotsikl. Soedin., No. 9, 1263 (1980).
Ya. V. Ogle, L. Kh. Baumane, P. A. Gavar, V. P. Kadysh, Ya. P. Stradyn', V. K. Lusis, D. Kh. Mutsenietse, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 5, 651 (1984).
I. É. Kirule, D. Ya. Rubene, É. A. Bisenieks, G. D. Tirzit, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 3, 416 (1982).
Ya. V. Ogle, L. Kh. Baumane, Ya. P. Stradyn', G. Ya. Dubur, V. P. Kadysh, R. A. Gavar, and V. K. Lusis, Khim. Geterotsikl. Soedin., No. 8, 1099 (1985).
J. R. Prous, The Years News. Therapeutic Targets, Prous Science Publishers, Barcelona (1994).
J. A. Derson and E. Brown, J. Am. Chem. Soc.,77, 447 (1955).
L. Baumane, J. Stradins, R. Gavars, and G. Duburs, Electrochim. Acta,37, No. 14, 2599 (1992).
Ya. P. Stradyn', I. Fol'ke, L. Kh. Baumane, V. Fol'kova, I. Klima, G. Ya. Dubur, and R. A. Gavar, Electrochemical Reduction of 4-(Nitroaryl)dihydropyridines. Cyclic Voltammetry and ESR Spectra of Electrochemically Generated Radical-Anions (Preprint) [in Russian], IOS Akad. Nauk LSSR (1985).
A. Alvarez-Lueje, L. J. Nunez-Vergara, and J. A. Squella, Electroanalysis,6, 259 (1994).
D. H. Geske, J. L. Ragle, M. A. Bambenek, and A. L. Balch, J. Am. Chem. Soc.,86, 987 (1964).
A. M. Triggle, E. Scheffer, and D. J. Triggle, J. Med. Chem.,23, 1442 (1980).
T. Fujinaga, Y. Deguchi, and K. Umemoto, Bull. Chem. Soc. Jpn.,37, 822 (1964).
L. G. Lawless, D. E. Bartak, and M. D. Hawley, J. Am. Chem. Soc.,91, 7121 (1969).
L. Hollek and D. Becher, J. Electroanal. Chem.,4, 321 (1962).
L. Kh. Baumane, Ya. P. Stradyn', R. A. Gavar, A. P. Gaukhman, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 11, 1494 (1988).
B. A. Vigante, Ya. Ya. Ozols, M. I. Terekhova, É. S. Petrov, G. Ya. Dubur, É. É. Liepin'sh, and G. I. Rozentale, Khim. Geterotsikl. Soedin., No. 4, 491 (1986).
T. I. Vakul'ska, L. I. Larina, O. B. Nefedova, and V. A. Lopyrev, Khim. Geterotsikl. Soedin., No. 4, 523 (1982).
V. P. Kadysh, G. Ya. Dubur, Ya. P. Stradyn', and Ya. R. Uldrikis, Khim. Geterotsikl. Soedin., No. 5, 641 (1978).
R. B. Ayscough, F. P. Sargent, and R. Wilson, Zh. Strukt. Khim. B, 903 (1966).
W. Kemula and Z. Kublik, Roczn. Chem.,32, 941 (1958).
V. F. Starichenko, V. A. Ryabinin, and S. M. Shein, Izv. Akad. Nauk. Ser. Khim., 520 (1976).
Landolt-Börnstein, Zahlenwerten und Funktionen aus Naturwissenschaften und Technik. Neue Serie, Springer Verlag, Berlin (1980), Gr. II, Vol. 9, Part d1, p. 538.
J. E. Biaglow, O. F. Nygaard, and C. L. Greenstock, Biochem. Pharmacol.,25, 393 (1976).
G. D. Tirzit, I. É. Kirule, L. Kh. Baumane, R. A. Gavar, Ya. P. Stradyn', and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 8, 1120 (1984).
U. Eisner and J. Kuthan, Chem. Rev.,72, 1 (1972).
A. É. Sausin', V. K. Lusis, G. Ya. Dubur, and Yu. I. Beilis, Khim. Geterotsikl. Soedin., No. 11, 1508 (1978).
D. Kh. Mutsenietse, V. K. Lusis, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 9, 1225 (1982).
Yu. M. Kargin, V. V. Kondranina, and N. I. Semakhina, Izv. Akad. Nauk. Ser. Khim., 178 (1971).
Ya. P. Stradyn', R. A. Gavar, and L. Kh. Baumane, Izv. Akad. Nauk Latv. SSR, No. 2, 73 (1986).
L. M. Baider, R. A. Gavar, B. Ya. Liberman, A. B. Rozenblit, Ya. P. Stradyn', P. É. Tomson, and M. B. Fleisher, Teor. Éksp. Khim.,15, 588 (1979).
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Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 219–233, February, 1997.
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Baumane, L., Gavar, R., Stradyn', Y. et al. Electrochemical reduction of 4-(nitrophenyl)-1,2- and 4-(nitrophenyl)-1,4-dihydropyridines and the ESR spectra of the obtained free-radical particles. Chem Heterocycl Compd 33, 190–201 (1997). https://doi.org/10.1007/BF02256761
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DOI: https://doi.org/10.1007/BF02256761