Asymmetric 3, 5-diaryl substituted 4H-1, 2, 6-thiadiazin-4-ones can be prepared from 3, 5- dichloro-4H-1, 2, 6-thiadiazin-4-one (1) via a multi-step protocol: selective nucleophilic mono-chloro substitution gives either the mono-methoxy or benzyloxy substituted mono- chlorothiadiazinones that can be phenylated via Suzuki–Miyaura coupling. Subsequent BBr3 mediated dealkylation gives 3-hydroxy-5-phenyl-4H-1, 2, 6-thiadiazin-4-one (9) that ...