THE STRUCTURE AND REACTIONS OF 4-PHENYL-5-HYDROXY-5,6-DIHYDRO-1,3,4-THIADIAZINE

Abstract

4-Phenyl-5-hydroxy-5,6-dihydro-1,3,4-thiadiazine 1 was prepared by the reduction of 4-phenyl-5-oxo-5,6-dihydro-1,3,4-thiadiazine 4 using lithium aluminum hydride (LAH). The structure of 1 was investigated by ¹H-NMR, ¹³C-NMR and UV spectroscopies and X-ray analysis. Treatment of 1 with alcohols, thiols and amines gave the corresponding 5-alkyloxy-, 5-alkylthio- and 5-alkylamino-4-phenyl-5,6-dihydro-1,3,4-thiadiazines 2 in almost quantitative yields. The mechanism of formation of 2 is discussed.