Studies and X-ray Determinations with 2-(Acetonylthio)benzothiazole: Synthesis of 2-(Benzothiazol-2-ylthio)-1-phenylethanone and 2-(Acetonylthio)Benzothiazole by C-S Bond Cleavage of 2-(Acetonylthio)benzothiazole in KOH

摘要

New route for the synthesis of 2-(benzothiazol-2-ylthio)-1-phenylethanone (6) and 2-(acetonylthio)benzothiazole (1) by using phenacyl bromide and α-chloroacetone, respectively, through carbon–sulfur bond cleavage reactions in a basic medium has been generated. Treatment of 1 with malononitrile and elemental sulfur afforded the corresponding derivative of 2-amino-3-cyanothiophene (12), whereas treatment of 1 with cyanoacetohydrazide afforded the corresponding derivative of cyanoacetylhydrazone derivative (13). The structure of the synthesis compounds has been established on the basis of elemental analyses, ~1H-NMR, ~(13)C-NMR, correlation spectroscopy, heteronuclear single quantum coherence, MS spectra, and X-ray crystallographic investigations.