Abstract
Bromination and iodation of 2-(alkenylthio)pyrimidin-6-ones occur selectively and lead to formation of the corresponding 7-oxo-2,3-dihydrothiazolopyrimidinium or 8-oxo-3,4-dihydro-2H-pyrimidothiazinium salts. The selectivity of the reaction is controlled by the nature of the alkenyl substituent on the sulfur atom and the basicity of the N(1) and N(3) atoms of the pyrimidine ring. The iodation reaction rate increases as the basicity of the N(3) atom increases.
Similar content being viewed by others
REFERENCES
D. G. Kim and V. I. Shmygarev, Khim. Geterotsikl. Soedin., 211 (1995).
P. Wippich, H. Guetschow, and S. Leistner, Synthesis, 714 (2000).
R. I. Vas'kevich, S. M. Kripak, V. I. Staninets, Yu. L. Zborovskii, and A. N. Chernega, Zh. Org. Khim., 36, 1091 (2000).
V. I. Staninets and E. A. Shilov, Usp. Khim., 40, 491 (1971).
M. M. Heravi, K. Aghapoor, and M. A. Nooshabadi, Synth. Commun., 28, 233 (1998).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Slivka, N.Y., Gevaza, Y.I. & Staninets, V.I. Halocyclization of Substituted 2-(Alkenylthio)pyrimidin-6-ones. Chemistry of Heterocyclic Compounds 40, 660–666 (2004). https://doi.org/10.1023/B:COHC.0000037323.22839.9f
Issue Date:
DOI: https://doi.org/10.1023/B:COHC.0000037323.22839.9f