複素環化合物のチオシアノ化反応に関する研究(第1報) : 2-置換チアゾール誘導体のチオシアノ化反応

抄録

Thiocyanation of 2-alkylamino-(I), 2-N-methylacetamido-(III), 2-imino-(V), 2-acetylimino-(VII), 2-hydroxy-(IX), 2-oxo-(XI), 2-mercapto-(XIII), 2-alkylthio (XV), 2-alkylsulfonyl-(XVII), and 2-thioxothiazoles-(XXIII) was studied. Thiocyanation was carried out by the bromine method using bromine and potassium or ammonium thiocyanate and by the urea method using monochlorourea in place of bromine. The reaction proceeded in the cases of I, III, VIII, IX, XI, and XV, giving 5-thiocyanato derivatives in a good yield, but no thiocyanated product was obtained from the reaction of V, VIII, XVII, and XXIII. Generally the urea method gave better results than the bromine method. 2-Alkylsulfonyl (or 2-arylsulfonyl)-5-thiocyanatothiazoles (XXI) were synthesized by oxidation of the corresponding 2-alkylthio (or 2-arylhio)-5-thiocyanatothiazoles (XVI) with an excess of peracetic acid.