R. Bleackley, A. S. Jones, R. Walker
1976
Citations
0
Influential Citations
31
Citations
Journal
Tetrahedron
Abstract
Abstract 5-Acetyluracil ( 1 ) has been converted into 5-(bromoacetyl)-uracil ( 2 ) by an established procedure. Reduction of 2 with sodium borohydride gave 5-(2-hydroxyethyl)uracil ( 4 ) in low yield. Treatment of 5-vinyluracil ( 7 ), obtained from 1 by published methods, with 1 molecular proportion of bromine followed by heating to 100°, gave E -5-(2-bromovinyl)uracil ( 8 ). Reaction of 8 with potassium t-butoxide gave 5(7)H-furanol[2,3,d]pyrimidin-6-one ( 10 ) and upon reduction with sodium in liquid ammonia, 8 gave 5-ethyluracil ( 11 ). Compound 2 showed low antibacterial activity against Staphylocuccus aureus , Streptococcus faecalis and Escherichia coli in nutrient broth and in a medium containing only inorganic salts, glucose and thymine, appreciable activity (∼ 6 μg/ml) against E. coli . Compound 2 was not incorporated into the DNA of E. coli .