Abstract
The acylation of 2-aminoquinazol-4-one by unsaturated acid chlorides proceeds principally at the exocyclic nitrogen atom and is complicated in the case of acryloyl chloride by a further intramolecular condensation forming 1,2,3,4-tetrahydropyrimido(2,1-b)quinazolin-2,6-dione. A lower acylation temperature using methacryloyl chloride leads to accumulation of 1-methacryloyl-2-aminoquinazol-4-one in the reaction mixture.
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Kh. M. Shakhidoyatov, L. M. Yun, and Ch. Sh. Kadyrov, Khim. Geterotsikl. Soedin., 1, 105 (1978).
A. R. Katritzky and C. W. Rees (eds.), Comprehensive Heterocyclic Chemistry, Vol. 3, Pergamon Press, Elmsford, NY (1984), p. 65.
A. R. Katritzky (ed.), Physical Methods in Heterocyclic Chemistry, Academic Press, New York, [Russian translation, Khimiya, Moscow, Leningrad (1966), p. 124].
P. Grammaticakis, Compt. Rend., 247, 2013 (1958).
H. Nakao and S. Sunagawa, Chem. Pharm. Bull., 13, 465 (1965).
D. I. Brown, B. T. England, and J. S. Harper, J. Chem. Soc., N 13, 1165 (1966).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1527–1531, November, 1987.
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Yun, L.M., Nazhimov, K.O., Masharipov, S. et al. Acylation of 2-aminoquinazol-4-ones by unsaturated acid chlorides. Chem Heterocycl Compd 23, 1222–1226 (1987). https://doi.org/10.1007/BF00479374
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DOI: https://doi.org/10.1007/BF00479374