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Synthèse et réactions de didésoxy‐5,6‐halogéno‐6‐α‐D‐ xylo ‐hepténo‐5‐furannurononitriles . Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Martin Olivier R.
Publication year - 1977
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.19770600231
Subject(s) - chemistry , ethylenediamine , oxazolidine , ring (chemistry) , enamine , hydrolysis , medicinal chemistry , ethanolamine , stereochemistry , organic chemistry , catalysis
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.