1394178-22-3

Upstream product

• 1394178-21-2 3-phenyl-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one 
• 1394178-20-1 3-hydroxy-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-18-7 3-(benzyloxy)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-17-6 3-methoxy-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1338699-66-3 3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one 
• 960-16-7 tributylphenylstannane 

Downstream Products

• 1394178-28-9 3-(4-chlorophenyl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-26-7 3-(4-methoxyphenyl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-27-8 3-(3-nitrophenyl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-25-6 3-(2-methoxyphenyl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-31-4 3-(fur-2-yl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 
• 1394178-29-0 3-phenyl-5-(thien-2-yl)-4H-1,2,6-thiadiazin-4-one 
• 1394178-30-3 3-(1-methyl-1H-pyrrol-2-yl)-5-phenyl-4H-1,2,6-thiadiazin-4-one 

Relevant academic research and scientific papers

Synthesis of asymmetric 3,5-diaryl-4H-1,2,6-thiadiazin-4-ones via Suzuki-Miyaura and Stille coupling reactions

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 can be activated by a modified Finkelstein halodehydroxylation via the triflate, enabling further arylation reactions using Suzuki-Miyaura or Stille coupling chemistry.

Selective stille coupling reactions of 3-chloro-5-halo(pseudohalo)-4 H -1,2,6-thiadiazin-4-ones

A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6- thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemose