90476-17-8Relevant articles and documents
Triazene Drug Metabolites. Part 5. A Simple Direct Synthesis of 3-Alkoxymethyl- and 3-Alkylthiomethyl-1-aryl-3-alkyltriazenes from 1-Aryl-3-hydroxymethyl-3-alkyltriazenes.
Iley, Jim,Rosa, Eduarda,Fernandes, Leonor
, p. 2216 - 2229 (2007/10/02)
Reaction of 1-aryl-3-hydroxymethyl-3-methyltriazenes with an alcohol in the presence of hydrogen chloride under anhydrous conditions gives rise to the corresponding 1-aryl-3-alkoxymethyl-3-methyltriazenes in excellent yield.The reaction is acid catalysed and probably proceeds through a triazenyliminium ion.Alkylthio derivatives can also be formed from thiols, but the synthesis fails for both amines, and alcohols containing an amino group.
OPEN-CHAIN NITROGEN COMPOUNDS. PART V. HYDROXYMETHYLTRIAZENES: SYNTHESIS OF SOME NEW ALKYL HOMOLOGUES OF THE ANTI-TUMOUR 3-METHYL-3-HYDROXYMETHYLTRIAZENES AND PREPARATION OF THE DERIVED ACETOXYMETHYL-, BENZOYLOXYMETHYL-, AND METHOXYMETHYLTRIAZENES
Hemens, Chantal M.,Manning, Hartford W.,Vaughan, Keith,LaFrance, Ronald,Tang, York
, p. 741 - 748 (2007/10/02)
The synthesis of some new 1-aryl-3-alkyl-3-hydroxymethyltriazenes is described.The method of coupling a diazonium salt with an alkylamine/formaldehyde mixture has been extended to (a) some diazonium ions with para substituents other than -M groups, (b) those with substituents in ortho position, and (c) to homologous alkylamines (e.g. ethylamine, propylamine, etc.).Hydroxymethyltriazenes can also be prepared by the reaction of a 1-aryl-3-methyltriazene with formaldehyde.Several new derivatives of hydroxymethyl function have been prepared.Reaction with acetic anhydride or benzoyl chloride in pyridine affords respectively the acetoxymethyl- and benzoyloxymethyl-triazenes; the acetates and benzoates react readily with methanol to give the novel methoxymethyltriazenes.This is the first report of a series of dialkyltriazenes with an ether linkage in the α position. An ether of this type has also been obtained directly from the diazonium fluoroborate salt by coupling with a mixture of benzylamine and formaldehyde in ethanolic solution.