Beilstein J. Org. Chem.2013,9, 135–146, doi:10.3762/bjoc.9.16
degree) were obtained. Pure 3-N-(glycosyl)oxadiazolinethiones can also be selectively obtained from glycosylsulfanyloxadiazoles by the thermal S→N migration of the glycosyl moiety, which is proposed to occur by a tight-ion-pair mechanism. Thermal S→N migration of the glycosyl moiety can be used for
: glycosyloxadiazolinethiones; glycosylsulfanyloxadiazoles; glycosylthiosemicarbazides; thermal rearrangement; X-ray crystallography; Introduction
Modified nucleosides are versatile motifs for studying the relationship between the structure and functions of nucleic acids and problems of metabolism, besides their main
→N migration of the glycosyl moiety in glycosylsulfanyloxadiazoles. (Benzylindolyl)glycosylsulfanyl-1,3,4-oxadiazoles could be thermally rearranged into the corresponding N-glycosides. These may either be converted into the corresponding (benzylindolyl)-2-N-(glycosyl)thiosemicarbazides (of type II
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Graphical Abstract
Scheme 1:
Structures of the different glycosylthiosemicarbazides.