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Triazene

About: Triazene is a research topic. Over the lifetime, 759 publications have been published within this topic receiving 8714 citations. The topic is also known as: Triazene cleavage & 1-triazene.


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Journal ArticleDOI
TL;DR: In this paper, the reaction of diazotized anthranilate esters with primary aliphatic amines has been reinvestigated, giving rise to a new series of comparatively unstable 1-alkyl-3-(o-carbalkoxyphenyl)-triazenes (3).
Abstract: The reaction of diazotized anthranilate esters with primary aliphatic amines has been reinvestigated, giving rise to a new series of comparatively unstable 1-alkyl-3-(o-carbalkoxyphenyl)-triazenes (3). The structures of the products have been confirmed by spectroscopic analysis, molecular ion mass measurements, and from the results of chemical degradation. The spectroscopic properties indicate a preference for the tautomer in which the azo-group is non-conjugated with the benzene ring, Ar•NH•N=N•R; this hypothesis is partly supported by the chemical degradation. In general, the triazenes (3) break down by fragmentation of the triazene moiety to give anthranilic acid derivatives, or undergo cyclization to 3-alkyltriazinones (1). The alkyltriazinones are also obtained directly in the coupling reaction of the diazonium salt with the amine in the presence of a sodium acetate buffer. The cyclization is quantitative when catalyzed by activity V alumina; a wide variation in the product distribution obtained by r...

24 citations

Journal ArticleDOI
TL;DR: In this paper, a new optical sensor for highly sensitive and selective determination of mercury(II) ion in aqueous solutions is developed, which has a relatively fast response time of less than 5 min.

24 citations

Journal ArticleDOI
TL;DR: A novel N5-linear energetic moiety of pentazadiene has been constructed for the first time from a triazene precursor in moderate to high yields by treatment of 1,3-bis(tetr-azol-5-yl)triazenes with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

24 citations

Journal ArticleDOI
TL;DR: In this paper, photosensitive polyetherurethane cationomers based on poly(tetramethylene oxide) diol of 2,000 average molecular weight, tolylene-2,4-diisocyanate, and N-methyldiethanolamine/triazene diols, as cochain extender, followed by a quaternization with benzyl chloride, were synthesized and characterized.
Abstract: New bifunctional triazene compounds 1-(m- hydroxymethyl)phenyl-3-(2-hydroxyethyl)-3-methyltriaz(1)ene and l-p-nitrophenyl-3,3-di(2-hydroxyethyl)triaz(1)ene as intermediates in polyurethane synthesis were prepared. Photosensitive polyetherurethane cationomers based on poly(tetramethylene oxide) diol of 2,000 average molecular weight, tolylene-2,4-diisocyanate, and N-methyldiethanolamine/triazene diols, as cochain extender, followed by a quaternization with benzyl chloride, were synthesized and characterized. Upon UV irradiation, feniltriazene chromophore in monomer and both polymers (ionomeric or nonionomeric type) is irreversibly cleaved, as evidenced in photolytic and kinetic studies. The rate constant of photolysis in ionomer film was lower than for the corresponding nonionic film. A positive pattern can then be developed by treatment with CHCl3 that dissolves the exposed zone, while the unexposed area remains resistant and insoluble. By incorporating side nitrofeniltriazene groups, photostable polyurethanes were obtained. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 88: 1203–1210, 2003

24 citations

Journal ArticleDOI
TL;DR: In vivo-in vitro bioassay experiments suggest that the (hydroxymethyl)triazenes exert their in vivo antitumor activity via the degradation product, the alkyltriazene, which is the product of hydrolysis in solution.
Abstract: 1-Aryl-3-(hydroxymethyl)-3-alkyltriazenes [ArN = NN(CH3)CH2OH] have been synthesized by diazonium coupling to the carbinolamine (RNHCH2OH), generated in situ from the alkylamine and formaldehyde mixtures. The (hydroxymethyl)triazene structure has been confirmed by IR, NMR, and mass spectral analysis and also by the preparation of a crystalline benzoate derivative. The mass spectra of the (hydroxymethyl)triazenes suggest that they fragment by loss of formaldehyde to give the methyltriazene, which is also the product of hydrolysis in solution. The degradation of the (hydroxymethyl)triazenes in solution has been followed by UV spectroscopy and by HPLC analysis, and the half-lives were determined under a variety of conditions. The half-lives of the corresponding methyl- and (hydroxymethyl)triazenes are very similar. Both methyl- and (hydroxymethyl)triazenes decompose on silica plates during TLC analysis to give products consistent with known diazo-migration reactions. The (hydroxymethyl)triazenes have pronounced antitumor activity against the TLX5 tumor in vivo; in vivo-in vitro bioassay experiments suggest that the (hydroxymethyl)triazenes exert their in vivo antitumor activity via the degradation product, the alkyltriazene.

24 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20236
202223
202116
202015
201917
201813