Abstract
3-Hydroxy-5-hydroxymethyl-2-methylpyridine (4-norpyridoxine) has been synthesized by the heterodiene condensation of 4-methyl-5-propoxyoxazole and 5-ethoxy-2,5-dihydrofuran-2-one through the stage of 3-hydroxy-2-methylpyridine-5-carbaldehyde with reduction of the latter by NaBH4. One of the isomeric adducts has been isolated, and its stereochemistry has been established by PMR spectroscopy.
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M. Ya. Karpeiskii and V. L. Florent'ev, Usp. Khim., 38, 1244 (1969).
G. O. Schenck, Ann., 64, 12 (1952).
T. Naito, K. Ueno, M. Sano, Y. Omura, I. Itoh, and F. Ishikawa, Tetrahedron Lett., 5767 (1968).
R. A. Firestone, E. E. Harris, and W. Reutor, Tetrahedron, 23, 943 (1967).
T. Yoshikawa, F. Ishikawa, Y. Omura, and T. Naito, Chem. Pharm. Bull., 13, 873 (1965).
N. A. Drobinskaya, L. V. Ionova, M. Ya. Karpeiskii, and V. L. Florent'ev, Khim. Geterotsikl. Soedin., 356 (1971).
V. L. Florent'ev, N. A. Drobinskaya, L. V. Ionova, and M. Ya. Karpeiskii, Khim. Geterotsikl. Soedin., 1028 (1969).
L. A. Perez-Medina, R. P. Mariella, and S. M. McElvain, J. Amer. Chem. Soc., 69, 2574 (1947).
D. B. McCormick and E. E. Snell, J. Biol. Chem., 236, 2085 (1961).
R. W. Burd, V. W. Rodwell, and E. E. Snell, J. Biol. Chem., 235, 1164 (1960).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 100–103, January, 1974.
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Chekhun, V.P., Zvonkova, E.N., Struchkova, M.I. et al. Synthesis of 4-norpyridoxine (3-hydroxy-5-hydroxymethyl-2-methylpyridine). Chem Heterocycl Compd 10, 88–91 (1974). https://doi.org/10.1007/BF00475917
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DOI: https://doi.org/10.1007/BF00475917