Reaktionen von Tosyl- bzw. Mesyl-Derivaten in der Morphin-Reihe, 9. Mitt.: Die Darstellung von Isothiocyanato-Derivaten

摘要

By reacting 6-O-tosyl codeine or 3-O-acetyl-6-O-tosyl morphine with KSCN in acetone the hitherto unknown 8-deoxy-8-isothiocyanato-pseudocodeine (1) and 3-O-acetyl-8-deoxy-8-isothiocyanato-pseudomorphine respectively were prepared. Treatment of the products with NaOCH3yields N-alkylthiocarbaminic acid esters. Asymmetrically substituted thiocarbamides were obtained by reaction of 8-deoxy-8-isothiocyanato-pseudocodeine with various amines, and a thiosemicarbazide by reaction with hydrazine.