Articles / Άρθρα

The Buchwald-Hartwig Pd-catalyzed C-N coupling reaction of 5-substituted 3-chloro-4H-1,2,6-thiadiazin-4-ones with primary (het)arylamines is described, affording twenty new 3,5-disubstituted 4H-1,2,6-thiadiazin-4-ones in 56–99% yield. The protocol enables the mild preparation of difficult to access 3,5-dianilino-1,2,6-4H-thiadiazin-4-ones. The reaction scope and limitations are discussed.

Treatment of 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazine (2) with selected alkanols, arenols and thiols led to regiospecific substitution of both geminal C-4 chlorines resulting in the formation of ketal or thioketal 3,5-dichloro-4H-1,2,6-thiadiazines 8a–h in 31–97% yields.