ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enamino- and Halogenoacetylenic sugarsTraitment of an aldehydosugar (1) with secondary amines gave in an essentially quantitative yield the expected enamines (4-6). Chloro- and bromo-acetylenic sugars (11-14) were obtained in good yields by reacting with lithium methylphenylamide the corresponding gem-dihalo-olefinic sugars (7-10), whereas a Z-gem-fluoro-enamine (17) was formed when the difluoro-olefinic sugar 15 was submitted to the same reaction. The fluoro-enamine 17 is a useful synthetic intermediate allowing the preparation of several kinds of C-glycosylic compounds bearing heterocycles like isoxazole, chromone or coumarin.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19760590325