Synthesis and antivirus activity of 1,3,5‐triazine derivatives

Reaction of 6‐phenyl‐4‐thioxo‐1,3,5‐triazine‐2‐one with alkyl halide in the presence of 1 equiv. of sodium hydroxide resulted in 4‐alkylthio‐6‐phenyl‐1,3,5‐triazine‐2‐one in good yield, whereas the above reaction provided 2‐alkoxyl‐4‐alkylthio‐6‐phenyl‐1,3,5‐triazine in the presence of 2 equiv. of sodium hydroxide. 6‐Phenyl‐4‐thioxo‐1,3,5‐triazine‐2‐one was oxidized with hydrogen peroxide to give 6‐phenyl‐1,3,5‐triazine‐2,4‐dione. Further treatment with ethyl bromoacetate or (substituted) benzyl bromides yielded 2,4‐dialkoxy‐6‐phenyl‐1,3,5‐triazines. At the same time, a small amount of 2‐dimethylamino‐4‐alkoxy‐6‐phenyl‐1,3,5‐triazines were isolated. Preliminary bioassays indicate that the title compounds possess good activities against tobacco mosaic virus. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:542–545, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10189