90475-99-3Relevant academic research and scientific papers
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.
