Abstract
The interaction of methyl 3-oxo-4-(phenylthio)butyrate with formaldehyde and ammonium acetate yielded 5-methoxycarbonyl-6-oxo-7-phenylthio-1,3-diazaadamantane, which, on being heated with skeletal nickel in isopropanol was converted into 6-hydroxy-5-methoxycarbonyl-1,3-diazaadamantane. The structures of the compounds have been confirmed by IR and PMR spectroscopy.
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A. I. Kuznetsov, B. A. Kamaritskii, V. Ya. Vainshtein, and B. V. Unkovskii, Zh. Obshch. Khim., 12, 227 (1976).
J. Kuthan and J. Palecek, Collect. Czech. Commun., 28, 2261 (1963).
P. F. Yakushev, A. I. Kuznetsov, V. V. Tolstikov, and B. V. Unkovskii, Zh. Obshch. Khim., 13, 2542 (1977).
K. Hiroi, Y. Matsuda, and S. Sato, Synthesis, 621 (1979).
T. Kato, M. Sato, and H. Kimura, J. Chem. Soc., Perkin Trans. I, 529 (1979).
A. I. Kuznetsov, P. F. Yakushev, and B. V. Unkovskii, Zh. Obshch. Khim., 10, 841 (1974).
H. Stetter, K. Dieminger, and E. Rauscher, Chem. Ber., 92, 2057 (1951).
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For Communication 2, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 661–663, May, 1985.
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Kuznetsov, A.I., Boiko, I.P., Sokolova, E.B. et al. Heteroadamantanes and their derivatives. 3. The synthesis of 6-hydroxy-5-methoxycarbonyl-1,3-diazaadamantane. Chem Heterocycl Compd 21, 557–559 (1985). https://doi.org/10.1007/BF00506073
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DOI: https://doi.org/10.1007/BF00506073