Abstract
A study, has been made of the interaction of N-(3-oxoalk),l)carbamates and -dithiocarbamates with sodium borohydride; it has been shown that, depending on the pH of the reaction medium, the interaction may produce either tetrahydro-1,3-oxazin-2-ones and -2-thiones, or N-(3-hydroxyalkyl)carbanartes and -dithiocarbamates.
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G. Stajer, A. E. Szabo, F. Fülöp, G. Bernath, and P. Sohar, Heterocycles,19, 1191 (l982).
G. Bernath, Gy. Göndös, K. Kovacs, and P. Sohar, Tetrahedron,29, 981 (1973).
G. Stajer, E. A. Szabo, F. Fülöp., G. Bernath, A. Kalman, Gy. Argay, and P. Sohar, Tetrahedron,39, 1829 (l983).
H. E. Zaugg, Synthesis, No. 2, 85 (1984).
A. S. Fisyuk and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 3, 416 (l991).
N. L. Allinger and V. L. Zalkov, J. Org. Chem.,25, 701 (1960).
B. V. Unkovskii, L. A. Ignatova, M. M. Donskaya, L. V. Andreeva, and L. L. Khoroshilova, Khim. Geterotsikl. Soedin., No. 6, 991 (1968).
A. S. Moskovkin, N. N. Guseva, L. A. Ignatova, I. V. Miroshnichenko, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 9, 1273 (1983).
A. S. Fisyuk, A. S. Moskovkin, I. V. Miroshnichenko, M. Ya. Bomikov, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 7, 985 (1992).
A. V. Peretokin, A. S. Moskovkin, I. V. Miroshnichenko, M. Ya. Botnikov, Yu. F. Malina, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 12, 1668 (1989).
A. B. Khasirdzhev, N. F. Korolenok, and B. V. Unkovskii, USSR Inventor's Certificate 423,796, Byull. Izobret., No. 4(1974).
A. V. Peretokin, A. S. Fisyuk, V. B. Rozhnov, and O. V. Agashkin, “Nucleophilic reactions of carbonyl compounds,” Mezhvuz. Nauchn. Sb., Saratov (1985), p. 116.
A. V. Peretokin, T. D. Sokolova, A. S. Fisyuk, Yu. F. Malina, and B. V. Unkovskii, USSR Inventor's Certificate 1,165,678, Byull. Izobret., No. 25 (1985).
T. Urbanski and A. Schmidt-Szalowska, Bull. Acad. Pol. Sci., Ser. Sci. Chim.,6, 447 (1976).
J. F. Willems, Fortschr. Chem. Forsch.,4, 554 (1963).
I. P. Boiko, Yu. F. Malina, O. I. Zhuk, Yu. Yu. Samitov, and B. V. Unkovskii, Zh. Org. Khim.,11, 605 (1975).
R. Lantsch and D. Arlt, Synthesis,11, 756 (1977).
M. Kahan, Monatsh. Chem.,26, 942 (1905).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, 260–265, February, 1994. Original article submitted November 15, 1993.
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Fisyuk, A.S., Ryzhova, E.V. & Unkovskii, B.V. Synthesis of tetrahydro-1,3-oxazin-2-ones and-2-thiones from esters of N-(3-oxoalkyl)carbamic and -dithiocarbamic acids. Chem Heterocycl Compd 30, 238–242 (1994). https://doi.org/10.1007/BF01165021
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DOI: https://doi.org/10.1007/BF01165021