Abstract
It is shown that the N-substituted derivatives of 4,5-diphenylimidazole, benzimidazole, naphth[1,2]imidazole, perimidine, and aceperimidine are hydroxylated by alkali metal hydroxides to give the corresponding 2-imidazolones and perimidones in high yields.
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Literature cited
A. E. Chichibabin, Zh. Russk. Khim. Obshchestva, 55, 7 (1923).
A. E. Chichibabin and A. I. Kursanova, Zh. Russk. Khim. Obshchestva, 62, 1211 (1930).
W. Koenigs, Ber., 12, 99 (1879).
W. Koenigs and W. Körner, Ber., 16, 2152 (1883).
O. Schickh, A. Binz, and A. Schulz, Ber., 69, 2593 (1936).
I. Eisch and H. Gilman, Chem. Rev., 57, 525 (1957).
A. F. Pozharskii, A. D. Garnovskii, and A. M. Simonov, Usp. Khim., 35, 261 (1966).
K. Hoffmann, Imidazole and Its Derivatives, New York (1953), p. 284.
R. L. Clark and A. A. Pessolano, J. Am. Chem. Soc., 80, 1657 (1958).
V. I. Minkin, Yu. A. Zhdanov, I. D. Sadekov, O. A. Raevskii, and A. D. Garnovskii, Khim. Geterotsikl. Soedin., 1100 (1967).
A. F. Pozharskii, A. M. Simonov, é. A. Zvezdina, and V. A. Anisimova, Khim. Geterotsikl. Soedin., 869 (1969).
A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., 111 (1970).
A. F. Pozharskii, A. M. Simonov, é. A. Zvezdina, and N. K. Chub, Khim. Geterotsikl. Soedin., 889 (1967).
A. M. Simonov and A. F. Pozharskii, Zh. Obshch. Khim., 33, 2350 (1963).
H. Vinot, Compt. Rend., 252, 899 (1961).
A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., 1129 (1970).
H. Biliz, Ber., 40, 4799 (1907).
I. Davoll and D. H. Laney, J. Chem. Soc., 314 (1960).
N. Ya. Turova and A. V. Novoselova, Usp. Khim., 36, 387 (1965).
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The material in this paper regarding the synthesis of perimidones and aceperimidones should be considered as communication V of our series entitled “Heterocyclic Analogs of Pleiadiene.“ See [16] for communication IV.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 124–128, January, 1971.
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Kashparov, I.S., Pozharskii, A.F. Direct hydroxylation of imidazoles. Chem Heterocycl Compd 7, 116–120 (1971). https://doi.org/10.1007/BF00477965
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DOI: https://doi.org/10.1007/BF00477965