Abstract
A convenient method is proposed for the synthesis of new derivatives of the pyridine series, alkyl N-(2-oxo-3-pyridyl)carbamates (IIa-i, IVa-j), in the reaction of 7-trifluoromethyl-5-phenyl-2-oxooxazolo[5,4-b]pyridines (I, IIIa-j) with alcohols.
Similar content being viewed by others
References
US Patent No. 3364225; Chem. Abs.,68, 59444 (1968).
R. L. Shriner and R. G. Child, J. Am. Chem. Soc.,74, 549 (1952).
J. R. Damewood, P. D. Edwards, Sc. Feeney, B. C. Gomes, G. B. Steelman, P. A. Tuthill, J. C. Williams, P. Warner, Sh. A. Woolson, D. J. Wolanin, and Ch. A. Veale, J. Med. Chem.,37, 3303 (1994).
P. R. Bernstein, D. Andisik, P. K. Brandley, Ch. B. Bryant, Ch. Ceccarelli, J. R. Damewood, R. Earley, P. D. Edwards, Sc. Feeney, B. C. Gomes, B. J. Kosmider, G. B. Steelman, R. M. Thomas, E. P. Vacek, Ch. A. Veale, J. C. Williams, D. J. Wolanin, and Sh. A. Woolson, J. Med. Chem.,37, 3313 (1994).
R. E. Damschroeder and D. L. Shriner, J. Am. Chem. Soc.,58, 1610 (1936).
P. A. Smith, Org. React.,3, 337 (1946).
Japanese Patent No. 58192860; Chem. Abs.,100, 15651n (1948).
Sang-Sup Jew, Hyeung Geun Park, Hee-Joo Park, Min-Soo Park, and Youn-Sang Cho, Tetrahedron Lett.,31, 1559 (1990).
R. Leardini and G. Zanardi, Synthesis, No. 3, 225 (1982).
É. Gudrinietse, M. Yure, P. Paspors, A. Karklinya, and É. Palitis, Khim. Geterotsikl. Soedin., No. 2, 271 (1995).
M. V. Yure, D. V. Shantare, and É. Yu. Gudrinietse, Khim. Geterotsikl. Soedin., No. 4, 542 (1996).
Ch. Flouzat, M. Blanchet, and G. Guillaumet, Tetrahedron Lett.,33, 4571 (1992).
A. F. Mishnev, S. V. Belyakov, Ya. Ya. Bleidelis, S. K. Apinitis, and É. Yu. Gudrinietse, Kristallografiya,31, 297 (1986).
S. V. Belyakov, A. F. Mishnev, Ya. Ya. Bleidelis, I. Ya. Plukse, and É. Ya. Gudrinietse, Zh. Strukt. Khim., No. 5, 169 (1988).
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. II, No. 12, S1 (1987).
W. P. Busing and H. A. Levy, Acta Crystallogr.,17, 142 (1964).
L. N. Kuleshova and P. M. Zorkii, Acta Crystallogr.,B37, 1363 (1981).
Yu. B. Zefirov and P. M. Zorkii, Zh. Strukt. Khim., No. 6, 994 (1976).
A. F. Mishnev and S. V. Belyakov, Kristallografiya,33, 835 (1988).
G. M. Sheldrick, in: Crystallographic Computing 6, H. D. Flack, L. Parkanyi, and K. Simon (eds.), IUCr and Oxford University Press (1993), p. 110.
Additional information
Riga Technical University, Riga LV-1048. Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 241–249, February, 1997.
Rights and permissions
About this article
Cite this article
Shantare, D., Yure, M., Belyakov, S.V. et al. 2-Oxooxazolopyridines. 1. Synthesis of alkyl N-(2-oxo-3-pyridyl)carbamates. Chem Heterocycl Compd 33, 208–215 (1997). https://doi.org/10.1007/BF02256763
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02256763