Facile syntheses of 1,2,4-triazole and s-triazine glycosides from glycosyl isothiocyanates.
Reaction of glycosyl isothiocyanates (la, b or c) with acyl or aroyl hydrazine gave the corresponding glycosyl thiosemicarbazides, and which were treated with Ac2O-H3PO4 to yield 1,2,4-triazole glycosides. Similar treatment of la, b or c with amidino compounds gave glycosylisothiobiurets, followed by N-bromosuccinimide (NBS) oxidation to give 1,2,4-triazole glycosides. Treatment of glycosylisothiobiurets with triethyl orthoformate gave the corresponding s-triazine glycosides.
D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008722:Methods; D013329:Structure-Activity Relationship; D013861:Thiocyanates; D014227:Triazines / Q000138:chemical synthesis*; D014230:Triazoles / Q000138:chemical synthesis*
D006027:Glycosides; D007202:Indicators and Reagents; D013861:Thiocyanates; D014227:Triazines; D014230:Triazoles