Synthesis of asymmetric 3,5-diaryl-4H-1,2,6-thiadiazin-4-ones via Suzuki-Miyaura and Stille coupling reactions
Date
2012Source
TetrahedronVolume
68Issue
36Pages
7380-7385Google Scholar check
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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 BBr 3 mediated dealkylation gives 3-hydroxy-5-phenyl-4H-1,2,6-thiadiazin-4-one (9) that can be activated by a modified Finkelstein halodehydroxylation via the triflate, enabling further arylation reactions using Suzuki-Miyaura or Stille coupling chemistry. © 2012 Elsevier Ltd. All rights reserved.
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