Topic
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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41 citations
TL;DR: The method described herein complements existing procedures for the preparation of aryl azides from the respective amino, triazene, and halide derivatives and it is expected that it will greatly facilitate copper- and ruthenium-catalyzed azide-alkyne cycloaddition reactions for the prepared of diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3-triazoles derivatives.
Abstract: We report the copper(II)-catalyzed conversion of organoboron compounds into the corresponding azide derivatives. A systematic series of phenylboronic acid derivatives is evaluated to examine the importance of steric and electronic effects of the substituents on reaction yield as well as functional group compatibility. Heterocyclic substrates are also shown to participate in this mild reaction while compounds incorporating B-C(sp(3)) bonds are unreactive under the reaction conditions. The copper(II)-catalyzed boronic acid-azide coupling reaction is further extended to both boronate esters and potassium organotrifluoroborate salts. The method described herein complements existing procedures for the preparation of aryl azides from the respective amino, triazene, and halide derivatives and we expect that it will greatly facilitate copper- and ruthenium-catalyzed azide-alkyne cycloaddition reactions for the preparation of diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3-triazoles derivatives.
40 citations
TL;DR: The cancer chemotherapeutic drug, 5-(3,3-dimethyl-1-triazeno) imidazole-4-carboxamide, is metabolised in rats to a structurally related product which was detected by thin-layer chromatography and has a lower mobility and a colour reaction that is indistinguishable from the parent compound.
40 citations
TL;DR: In this paper, a triazene linker was used for the solid phase synthesis of monocyclic β-lactams via the ester-enolate imine condensation.
Abstract: Liquid-phase studies concerning the solid-phase synthesis of monocyclic β-lactams via the ester-enolate imine condensation route have been conducted utilizing triazene esters 1 and 2 as model compounds. Esters were attached to benzylamine resin 6 by a triazene linker employing the respective diazonium salts. Immobilized ester-enolates 8 and 10 were reacted with various imines and imine precursors to give polymer-bound β-lactams 14 and 17 in different substitution patterns. Traceless cleavage from the triazene linker yields the desired β-lactams 16 and 19.
38 citations
TL;DR: Electrochemical studies demonstrated that grafting through the triazene modifier can successfully compete with existing protocols for DNA immobilization through the commonly used alkanethiol linkers and diazonium salts.
Abstract: A new DNA modifier containing triazene, ferrocene, and activated ester functionalities was synthesized and applied for electrochemical grafting and characterization of DNA at glassy carbon (GC) and gold electrodes. The modifier was synthesized from ferrocenecarboxylic acid by attaching a phenyltriazene derivative to one of the ferrocene Cp rings, while the other Cp ring containing the carboxylic acid was converted to an activated ester. The modifier was conjugated to an amine-modified DNA sequence. For immobilization of the conjugate at Au or GC electrodes, the triazene was activated by dimethyl sulfate for release of the diazonium salt. The salt was reductively converted to the aryl radical which was readily immobilized at the surface. DNA grafted onto electrodes exhibited remarkable hybridization properties, as detected through a reversible shift in the redox potential of the Fc redox label upon repeated hybridization/denaturation procedures with a complementary target DNA sequence. By using a methylene...
37 citations