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Enaminosucres et sucres halogénoacétyléniques . Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Baehler Bruno,
Bonenfant Alain
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590325
Subject(s) - chemistry , enamine , yield (engineering) , medicinal chemistry , organic chemistry , chromone , catalysis , materials science , metallurgy
Enamino‐ and Halogenoacetylenic sugars Traitment 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.