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Synthesis of Thiadiazolylaminoglycosides Through Ring Contraction of Triazinoglycosides Induced by [TBA‐Ox]
Author(s) -
Kikelj Vincent,
Julienne Karine,
Chalopin Thibaut,
Gouin Sébastien G.,
Evain Michel,
Deniaud David
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2232
Subject(s) - chemistry , contraction (grammar) , ring (chemistry) , stereochemistry , formic acid , organic chemistry , medicine
A new synthetic route to thiadiazolylaminoglycosides, by a ring expansion/ring contraction sequence of glycosyl triazines, has been developed. Two potential mechanisms of this oxidative ring contraction using [TBA‐Ox] are discussed. The more plausible involves formation of an oxatriazepane intermediate followed by loss of formic acid , ring opening , and subsequent recyclization.