Abstract
It has been established that the reaction of 5,6-dialkyl-2-pyridones with dimethyl acetylenedicarboxylate leads to esters of 2-ketopyridin-1-ylfuramic acids, which are readily hydrolyzed in the cold by aqueous solutions of alkalis. The ease of hydrolysis of the esters is apparently explained by intramolecular catalysis as a consequent of the nucleophilic participation of the oxygen of the pyridone ring.
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References
L. Paquette, J. Org. Chem., 30, 2107, 1965.
B. Thyagarajan and K. Rajagopalan, Tetrah., 19, 1483, 1963.
L. Bauer, Ch. Boll, and G. Wright, J. Het. Chem., 3, 393, 1966.
N. P. Shusherina, R. Ya. Levina, and N. D. Dmitrieva, Vestn. MGU, no. 5, 191, 1958.
N. P. Shusherina, Huang Hua-min, and R. Ya. Levina, ZhOKh, 33, 2829, 1963.
R. Acheson and P. Tasker, J. Chem. Soc. (C), 1542, 1957.
R. Acheson and G. Bond, J. Chem. Soc., 247, 1956.
R. Acheson and M. Burstall, J. Chem. Soc., 3240, 1954.
N. P. Shusherina, O. V. Slavyanova, N. I. Svetlova, and R. Ya. Levina, Vestuik MGU, Ser. khim. [Moscow University Chemistry Bulletin], no. 1, 97, 1969.
N. P. Shusherina, O. V. Slavyanova, and R. Ya. Levina, ZhOKh, 39, 1173, 1969.
N. P. Shusherina, T. Kh. Gladysheva, and R. Ya. Levina, Vestuik MGU, ser. khim. [MUC], no. 1, 101, 1968.
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Shusherina, N.P., Slavyanova, O.V., Rodionova, G.N. et al. δ-Lactones and δ-lactams. Chem Heterocycl Compd 6, 451–453 (1970). https://doi.org/10.1007/BF00478389
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DOI: https://doi.org/10.1007/BF00478389