Abstract
The acylation of 2-amino-5-phenyl-4-oxazolinone and 2-amino-1-methyl-4-imidazolinone with acetyl chloride in benzene in the presence of triethylamine leads to the formation of 2-acetamido-5-phenyl-4-oxazolinone and 2-acetamido-1-methyl-4-imidazolinone. The acylation of 2-amino-4-imidazolinone under the indicated conditions, as well as with acetic anhydride, gives 1-acetylimidazolidine-2,4-dione. 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione (dehydroacetic acid) is formed as a side product in the acylation of 2-amino-4-azolinones with acetyl chloride in benzene in the presence of triethylamine. The IR and PMR spectra of the compounds obtained are presented.
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Literature cited
A. A., Tsurkan, A. I. Frolova, N. I. Pospelov, and L. A. Dorofeeva, Khim.-farm. Zh., No. 6, 12 (1975).
S. M. Ramsh, Yu. G. Basova, A. I. Ginak, N. A. Smorygo, and A. A. Rodin, Khim. Geterotsikl. Soedin., No. 1, 30 (1982).
S. M. Ramsh, A. I. Ginak, N. A. Smorygo, Yu. G. Basova, and E. G. Sochilin, Zh. Org. Khim., 14, 1327 (1978).
W. Hansen and L. W. Masch, West German Patent No. 1237570; Chem. Abstr., 67, 64385 (1967).
H. R. Ing, R. A. Kerwick, and G. M. Richardson, J. Chem. Soc., No. 11, 2047 (1932).
S. N. Baranov, Zh. Obshch. Khim., 32, 1230 (1962).
A. T. Dren and R. S. Janicki, in: Pharmacological and Biochemical Properties of Drug Substances, Vol. 1, edited by M. E. Goldberg, Washington (1977), p. 33.
C. Lempert, Chem. Rev., 59, 667 (1959).
Yu. G. Basova, S. M. Ramsh, and A. I. Ginak, Khim. Geterotsikl. Soedin., No. 8, 1046 (1981).
H. Najer, J. Armand, J. Menin, and N. Voronine, Compt. Rend., C, 260, 4343 (1965).
C. F. Howell, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 27, 1686 (1962).
K. Matsumoto and H. Rapoport, J. Org. Chem., 33, 552 (1968).
H. Becker, Introduction to the Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow (1977), p. 323.
Beilstein, 17, 559 (1933).
Organic Syntheses [Russian translation], Collective Vol. 3, Inostr. Lit., Moscow (1952).
Organic Syntheses [Russian translation], Collective Vol. 3, Inostr. Lit., Moscow (1952), p. 150.
Houben-Weyl, Methoden der organischen Chemie, Vol. 4, Georg Thieme Verlag, Stuttgart.
E. C. C. Baly, J. N. Collie, and H. E. W. Watson, J. Chem. Soc., No. 156, 144 (1909).
C. H. Howell, N. Q. Quinones, and R. A. Hardy, J. Org. Chem., 27, 1679 (1962).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 601–604, May, 1983.
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Ramsh, S.M., Zheltonog, N.G., Shamina, L.P. et al. Acylation of 2-amino-5-phenyl-4-oxazolinone and 2-amino-4-imidazolinones. Chem Heterocycl Compd 19, 481–484 (1983). https://doi.org/10.1007/BF00514453
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DOI: https://doi.org/10.1007/BF00514453