作者
El Sayed H El‐Ashry, Nagwa Rashed, Laila F Awad, El Sayed Ramadan, Somia M Abdel‐Maggeed, Nagat Rezki
发表日期
2008/5/1
期刊
Journal of Carbohydrate Chemistry
卷号
27
期号
2
页码范围
70-85
出版商
Taylor & Francis Group
简介
Under microwave irradiation (MWI), 4‐phenyl‐5‐substituted‐4H‐1,2,4‐triazole‐3‐thiol derivatives 7 and 8 were synthesized in a good yield by intramolecular cyclization of the aroyl phenyl thiosemicarbazides 5 and 6. The respective triazolylglycosides (Str‐glycosides) 1217 were obtained by reaction of triazoles 7 and 8 with glycosyl halides 911 in dry acetone in the presence of potassium carbonate as base under both conventional and MWI conditions. Alkylation of 7 and 8 with haloalchols 18–20 in boiling ethanolic solution containing sodium ethoxide as a base gave the corresponding alkylated analogs 2126. MWI conditions led to higher yield in shorter reaction time than the conventional method. Treatment of 26 with tosyl chloride gave the unexpected product 29 and not 27 or 28. Oxidation of 26 with sodium metaperiodate afforded triazole 8 and not the aldehyde 30. Attempted glycosylation and alkylation …
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