Abstract
The ambident anion of 1-methyluracil gives with phenylbenzyhydrazonoyl chloride, depending on the conditions, the N-acylation product (polar solvent, room temperature), or the O-acylation product (nonpolar solvent, heating), which rearranges to a cytosine derivative. Convenient methods have been developed for the preparation of 6-methyl-1,3-diphenyl-5,6-dihydro-5-oxopyrimido[4,3-c]triazolium chloride, a fluorescent derivative of 1-methyluracil, from the N-acylation product, and for the rapid base cleavage of the uracil ring under very mild conditions.
Similar content being viewed by others
Literature cited
R. J. De Pasquale, Int. Eng. Chem., Prod. Res. Devel., 17, 278 (1978).
K. A. Cruickshank, J. Jiricny, and C. B. Reese, Tetrahedron Lett., No. 25, 681 (1984).
C. L. Angell, J. Chem. Soc., No. 2, 504 (1961).
D. Lipkin and E. G. Lovett, J. Org. Chem., 40, 1713 (1975).
G. W. H. Cheesman, C. J. Turner, and D. Brown, J. Org. Magn. Reson., 12, 212 (1979).
C. W. Whithead and J. J. Traverso, J. Amer. Chem. Soc., 82, 3971 (1960).
A. J. Elliott, M. S. Gibson, M. M. Kayser, and G. A. Pawelchak, Canad. J. Chem., 51, 4115 (1973).
A. J. Elliott, P. D. Callaghan, M. S. Gibson, and S. T. Nemeth, Canad. J. Chem., 53, 1484 (1975).
A. F. Heagarty, J. A. Kearney, M. P. Casman, and F. L. Scott, J. Chem. Soc., Chem. Commun., No. 13, 689 (1971).
A. F. Heagarty, J. A., Kearney, and F. L. Scott, J. Chem. Soc., Perkin 2, No. 10, 1422 (1973).
A. F. Heagarty, J. A. Kearney, and F. L. Scott, Tetrahedron Lett., No. 31, 3211 (1972).
A. P. Rozjivin, A. A. Kost, and V. N. Shibaev, Studia Biophysica, 51, 291 (1975).
H. C. Van der Plas, Ring Transformation of Heterocycles, Vol. 2, Academic Press, London (1973), p. 116.
E. G. Lovett and D. Lipkin, J. Org. Chem., 42, 2574 (1977).
E. G. Lovett and D. Lipkin, J. Org. Chem., 42, 1722 (1975).
T. Kametany, K. Sota, and M. Shio, J. Het. Chem., 7, 821 (1970).
P. W. Hicmott, Tetrahedron, 38, 3363 (1982).
J. L. Ripoll, H. Lebrum, and A. Thuiller, Tetrahedron, 36, 2497 (1980).
H. Ahlbrecht and W. Raab, Synthesis, No. 4, 320 (1983).
R. Knorr, P. Loew, and P. Kassel, Synthesis, No. 10, 785 (1983).
R. Stradi, P. Trimarco, and A. Vigevani, J. Chem. Soc., Perkin 2, No. 1, 1 (1978).
M. Ahmed and P. W. Hickmott, J. Chem. Soc., Perkin 2, No. 6, 838 (1977).
H. J. Jacobsen, S.-O. Lawesson, J. T. Marshell, G. Schrell, and D. H. Williams, J. Chem. Soc., B, No. 10, 940 (1966).
M. R. Atkinson, E. A. Parkes, and J. B. Polya, J. Chem. Soc., No. 6, 4256 (1954).
W. Szer and D. Shugar, In: Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1, Intersci. Publ, (1968), pp. 61, 110.
I. N. Zhmurova and V. G. Yurchenko, Zh. Obshch. Khim., 47, 1010 (1977).
L. C. Raiford and R. H. Manley, J. Org. Chem., 5, 590 (1940).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 649–655, May, 1986.
Rights and permissions
About this article
Cite this article
Chernyshova, N.B., Shibaev, V.N. Reaction of 1-methyluracil with phenylbenzhydrazonoyl chloride. Chem Heterocycl Compd 22, 532–538 (1986). https://doi.org/10.1007/BF00519534
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00519534