Abstract
The polarographic reduction of 1, 4-dihydropyridine-3, 5-dicarboxylic acid derivatives in dimethylformamide was studied. It is shown that the first diffusion waves of these compounds are irreversible one-electron waves and correspond to electrical reduction of the C=C bond of the conjugated system of the 1, 4-dihydropyridine ring to give a tetrahydro derivative. In the case of pyridine-3, 5-dicarboxylic acid esters partial dimerization of the resulting freeradical products occurs along with electron transfer. It is shown that the introduction of alkoxycarbonyl substituents in 2, 6-methyl and 3, 5-methoxycarbonyl groups and in the 4 position and of a carboxyl group in the 4 position facilitates the electrical reduction of the 1, 4-dihydropyridine ring. The introduction of a methyl group in the 4 position hinders reduction of the ring.
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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 (1975).
Ya. P. Stradyn', G. Ya. Dubur, Yu. I. Beilis, Ya. R. Uldrikis, A. É. Sausin', and B. S. Chekavichus, Khim. Geterotsikl. Soedin., No. 11, 1530 (1975).
V. Skala, J. Volke, V. Ohanka, and J. Kuthan, Coll. Czech. Chem. Commun.,42, 292 (1977).
U. Eisner and J. Kuthan, Chem. Rev.,72, 1 (1972).
T. A. Mikhailova, N. I. Kudryashova, and N. V. Khromov-Borisov, Zh. Obshch. Khim.,39, 26 (1969).
C. O. Schmakel, K. S. V. Santhanam, and P. J. Elving, J. Electrochem. Soc.,121, 1033 (1974).
P. H. Given, J. Chem. Soc., No. 8, 2684 (1958).
M. Maruyama and K. Murakami, Rev. Polarogr.,21, 59 (1975).
J. Kuthan, V. Simonek, V. Volkova, and J. Volke, Z. Chem.,11, 111 (1971).
J. Kuthan, J. Volke, V. Volkova, and V. Simonek, Coll. Czech. Chem. Commun.,39, No. 12, 3438 (1974).
S. G. Maironovskii, Catalytic and Kinetic Waves in Polarography [in Russian], Nauka, Moscow (1966), p. 205.
S. G. Mairanovskii, Ya. P. Stradyn', and V. D. Bezuglyi, Polarography in Organic Chemistry [in Russian], Khimiya, Leningrad (1975), pp. 83, 264.
V. D. Bezuglyi, Polarography in the Chemistry and Technology of Polymers [in Russian], Khimiya, Leningrad (1968), p. 66.
P. J. Brignell, U. Eisner, and P. G. Farrell, J. Chem. Soc. (B), No. 11, 1083 (1966).
H. O. House, E. Feng, and N. P. Peet, J. Org. Chem.,36, 2371 (1971).
R. Schiff and J. Puliti, Ber.,16, 1607 (1883).
W. Traber and P. Karrer, Helv. Chim. Acta,41, 2066 (1958).
Ya. R. Uldrikis, G. Ya. Dubur, I. V. Dipan, and B. S. Chekavichus, Khim. Geterotsikl. Soedin., No. 9, 1230 (1975).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 641–646, May, 1978.
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Kadysh, V.P., Dubur, G.Y., Stradyn, Y.P. et al. Electrochemical reduction of 1, 4-dihydropyridine-3, 5-dicarboxylic acid derivatives in an aprotic medium. Chem Heterocycl Compd 14, 524–529 (1978). https://doi.org/10.1007/BF00673336
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DOI: https://doi.org/10.1007/BF00673336