Synthesis of 5-substituted uracil derivatives.

The synthesis of a series of 5-substituted uracil derivatives is described. 5-Bromoacetyluracil (2a) was converted to the glycolyl (2b), glycyl (2c), N,N-dimethylglycyl (2d), 4-imidazolyl (3), and 2-amino-4-thiazolyl (4) derivatives. 5-Formyluracil (5) was used in the preparation of the 2-imidazolyl (6), the 3-acrylic acid (7b), the ester (7a), and the 3-N,N-dimethylacrylamide (8) derivatives. A Mannich reaction converted 5-acetyluracil to the amino ketone 9 which was reduced to give the 3-dimethylamino-1-propanol derivative 10. Compounds 2b,d,3,4,6, and 7b failed to inhibit the growth of Escherichia coli B and Staphylococcus aureus.