Abstract
The nitration of 6-phenyl-2-pyridone with 70% nitric acid, nitronium tetrafluoroborate, and acetyl nitrate has been studied for the first time. It was shown that, depending on the reaction temperature, the nitro group enters the 3 or 5 position of the heterocyclic ring. 3- Nitro-6-(p-nitrophenyl)-2-pyridone is formed by the action of fuming nitric acid on 6-phenyl-2-pyridone. The structures of the nitropyridones obtained were proved by PMR spectroscopy.
Similar content being viewed by others
Literature cited
O. Fischer and M. Chur, J. Prakt. Chem., 93, [2], 363 (1916).
A. E. Chichibabin and S. A. Shapiro, Zh. Russk. Fiz. Khim. Obshchestva, 53, 233 (1921).
A. Albert, J. Chem. Soc., 1020 (1960).
E. Klinsberg, Pyridine and Its Derivatives, New York-London (1961), p. 247; (1962), p. 666.
A. Burton, P. Halls, and A. Katritzky, Tet. Letters, 2211 (1971).
N. P. Shusherina, N. D. Dmitrieva, E. A. Luk'yanets, and R. Ya. Levina, Zh. Obshch. Khim., 33, 3434 (1963).
L. Paquette and W. Farley, J. Org. Chem., 32, 2725 (1967).
H. Hertog, D. Burman, and P. Villiers, Rec. Trav. Chim., 80, 325 (1961).
F. Broekmann and H. Tandelloo, Rec. Trav. Chim., 81, 107 (1962).
K. Schofield, Quart. Rev., 4, 382 (1950).
R. Selms, J. Org. Chem., 33, 478 (1968).
L. D. Smirnov, M. P. Avezov, V. P. Lezina, B. E. Zaitsev, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, 845 (1971).
C. Bonsall and J. Hill, J. Chem. Soc., C, 1836 (1967).
W. Pirkle and M. Dines, J. Heterocycl. Chem., 6, 1 (1969).
J. Leben, Ber., 29, 1675 (1896).
Author information
Authors and Affiliations
Additional information
See Zh. Organ. Khim., 7, 387 (1971) for communication V.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1374–1378, October, 1972.
Rights and permissions
About this article
Cite this article
Shusherina, N.P., Likhomanova, T.I. 2-Pyridones. Chem Heterocycl Compd 8, 1242–1245 (1972). https://doi.org/10.1007/BF00475539
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00475539