Synthesis and Some Reactions of 6- (2-Hydroxyphenyl) -2-thiouracils

6-(2-Hydroxyphenyl)-2-thiouracil (2a) and its 5-chloro and 5-bromo derivatives (2b, c) were synthesized by the reactions of 4-methoxycoumarin (1a) and 3-chloro- and 3-bromo-4-methoxycoumarins (1b, c), respectively, with thiourea in the presence of sodium ethoxide. In these reactions, compound 1c gave not only the pyrimidine 2c, but also the Perkin rearrangement product : N-(3-ethoxybenzofuran-2-carbonyl)thiourea (3). 2-Thiouracils 2a-c were converted to the uracil derivatives (6a, b). Reactions of 2a-c with some cyclic amines and the methylation of 2b, c with methyl iodide were also examined.