Nucleoside Derivatives of 1,2,4-Triazine Reaction of Some Derivatives of 1,2,4-Triazine with Tetra-O-acetyl-α-D-glucopyranosyl Bromide

Abstract

4,6-Diphenyl-, 6-phenyl-4-p-tolyl- and 6-styryl-4-phenyl-3-thioxo-5-oxo-2,3,4,5-tetrahydro-1,2,4-triazines (1 a-c) react with tetra-0-acetyl-α-D-glucopyranosyl bromide (2) to give the corresponding 2-tetra-0-acetyl-B-D-glucopyranosyl derivatives (4a-c), respectively. Oxidation of 4a with H2O2 gives the 3,5-dioxo derivative (7). On the other hand deacetylation of 4a affords 2-B-D-glucopyranosyl-4,6-diphenyl-3-thioxo-5-oxo-2,3,4,5-tetrahydro-1,2,4-triazine (8). Furfurylidene pyruvic acid condenses with 4-phenylthiosemicarbazide to give 6-furfurylidene-4-phenyl-3-thioxo-5-oxo-2, 3, 4, 5-tetrahydro-1, 2, 4-triazine (1d). 1d reacts with ethyl iodide to give the 3-ethylmercapto derivative (9), and reacts with 2 to give 4d.