N-2-Glycosyl Thiosemicarbazides from N-3-Glycosyl Oxadiazolinethiones Obtained from 2-S-Glycosyl Oxadiazolines via Mild Thermal S -> N Migration of the Glycosyl Moiety

作者：El Ashry El Sayed H^*; El Tamany El Sayed H; Aly Mohamed R E; Boraei Ahmed T A

来源：Synlett, 2010, 2010(15): 2247-2250.

DOI：10.1055/s-0030-1258024

• indolyloxadiazolines
• S-glycosides
• N-glycosides
• glycosylation
• thiosemicarbazides
• thermal rearrangement

A new class of N-2-glycosyl thiosemicarbazides has been synthesized from N-3-glycosyl oxadiazoline-thiones. Glycosylation of 5-(1H-indol-2-yl)-1,3,4-oxadiazolin-2(3H)-thione with acetylated alpha-glycosyl halides by grinding in the presence of basic alumina gave the S-glycosyl oxadiazoles while in the presence of Hg(II) chloride N-3 glycosyl analogues were obtained. In the presence of Et(3)N or K(2)CO(3), mixtures of S- and N-glycosylated isomers were obtained as products. The S -> N glycosyl migration under catalyst-free mild thermal conditions was described, and a new class of N-2-glycosyl thiosemicarbazides was synthesized from N-3-glycosyl oxadiazolinethiones by ring cleavage of the oxadiazolole ring by treatment with ammonia in methanol.

• 出版日期2010-9