Synthèse et réactions de didésoxy-5,6-halogéno-6-α-D-xylo-hepténo-5-furannurononitriles. Communication préliminaire

✍ Scribed by Jean M. J. Tronchet; Olivier R. Martin

• Publisher: John Wiley and Sons
• Year: 1977
• Tongue: German
• Weight: 272 KB
• Volume: 60
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19770600231

✦ Synopsis

Synthesis and reactions of 5,6‐dideoxy‐6‐halogeno‐α‐D‐xylo‐hept‐5‐eno‐furanurononitriles

The 5,6‐dideoxy‐6‐chloro‐, 6‐iodo‐ and 6‐fluoro‐3‐O‐methyl‐α‐D‐xylo‐hept‐5‐eno‐furanurononitriles have been prepared, their properties described as well as the methods used for the assignment of the configuration of the geometrical isomers. Some new reactions of the 6‐bromo analog (1) of these compounds are reported. For example, when reacted with 2‐mercaptoethanol or N,N′‐dimethyl‐ethylenediamine in the presence of NaOH, 1 gave the corresponding six‐membered ring, stereo‐isomers of an oxathiane or of a perhydrodiazine respectively. When the base used was Et~3~N and the binucleophile the N‐methyl‐ethanolamine or the N,N′‐dimethyl‐ethylene‐diamine the major product was a cyano‐enamine which could be hydrolysed to a β‐cyanoketone or cyclized to a five‐membered ring, an oxazolidine or an imidazolidine respectively.