73779-17-6Relevant academic research and scientific papers
OPEN-CHAIN NITROGEN COMPOUNDS. PART VI. THE FORMATION OF BIS(1-ARYL-3-METHYLTRIAZEN-3-YLMETHYL) METHYLAMINES IN THE REACTION OF DIAZONIUM IONS WITH MIXTURES OF FORMALDEHYDE AND METHYLAMINE
Manning, Hartford W.,Hemens, Chantal M.,LaFrance, Ronald J.,Tang, York,Vaughan, Keith
, p. 749 - 754 (2007/10/02)
The synthesis of a series of N,N-bis(1-aryl-3-methyltriazen-3-ylmethyl) methylamines from coupling diazonium salts with mixtures of methylamine and formaldehyde is described.These novel bis-triazenes, or heptazanonadienes, have significant anti-tumour activity against the TLX5 lymphoma in mouse.The mechanism of formation of these triazenes is discussed with reference to the implication to the presumed equilibria taking place in the methylamine/formaldehyde solution.The formation of the bis-triazene is usually accompanied by the formation of a 3-hydroxymethyltriazene, and it has been shown that the hydroxymethyltriazene can be transformed into the bis-triazene.The proportions of the two products are strongly influenced by the relative amounts of methylamine and formaldehyde.Coupling the p-bromobenzenediazonium salt to a 1:1 methylamine/formaldehyde mixture affords mainly the bis-triazene, whereas a 1:50 mixture gives almost totally the hydroxymethyl triazene.These results suggest that the two triazenes arise from diazonium coupling to different species in the amine/formaldehyde mixture; this hypothesis is supported by the formation of identical product mixtures from coupling the diazonium ion with (a) a 1:1 MeNH2/CH2O mixture, and (b) the cyclic trimer of the carbinolamine MeNHCH2OH, and by the identification of a minor product from the reaction of p-chlorobenzenediazonium fluoroborate with MeNH2/CH2O as bis(1-p-chlorophenyl-3-methyltriazen-3-yl) methane.
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.
N,N-Bis-(1-aryl-3-methyltriazen-3-ylmethyl)methylamines (1,9-Diaryl-3,5,7-trimethyl-1,2,3,5,7,8,9-hepta-azanona-1,8-dienes): Novel Coupling Products from the Reaction of Arenediazonium Ions with Methylamine and Formaldehyde
Lafrance, Ronald J.,Tang, York,Vaughan, Keith,Hooper Donald L.
, p. 721 - 722 (2007/10/02)
The reaction of arenediazonium ions with aqueous formaldehyde-methylamine solutions affords mixtures of the 3-hydroxymethyltriazenes, ArN=NN(Me)CH2OH, and the previously unreported bis(triazenylmethyl)methylamines, ArN=NN(Me)CH2N(Me)CH2N(Me)N=NAr.
Triazenes: A Reinvestigation of the Coupling Reaction between Aryldiazonium Ions and Methylamine/Formaldehyde Mixtures
Cheng, Shee C.,Sousa Fernandes, M. Leonor de,Iley, Jim,Rosa, M. Eduarda N.
, p. 1101 - 1113 (2007/10/02)
Aryldiazonium fluoroborates react with methylamine/formaldehyde mixtures to give bismethylamines rather than 1-aryl-3-hydroxymethyl-3-methyltriazenes as previously reported.Aryldiazonium chlorides react with methylamin
