74148-29-1Relevant academic research and scientific papers
Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions
Davis, Garrett J.,Townsend, Julia A.,Morrow, Madeline G.,Hamie, Mohamed,Shepard, Abigail J.,Hsieh, Chih-Chieh,Marty, Michael T.,Jewett, John C.
, p. 2432 - 2438 (2021/11/18)
This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified.
Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes
Schotten, Christiane,Leprevost, Samy K.,Yong, Low Ming,Hughes, Colan E.,Harris, Kenneth D. M.,Browne, Duncan L.
supporting information, p. 2336 - 2341 (2020/06/05)
A range of diazonium salts and their corresponding triazenes have been prepared in order to directly compare their relative thermal stabilities (via initial decomposition temperature) from differential scanning calorimetry (DSC) data. A structure-stability relationship has been explored to investigate trends in stability, depending on the aromatic substituent and the structure of the secondary amine component of the diazonium salts and triazenes. All of the triazenes investigated show significantly greater stability (many are stable above 200 °C) compared with the corresponding diazonium salts, which show varying stabilities.
Synthesis of triazenes of n-heterocycles mediated by resin immobilized diazonium ions
Das, Pranab J,Begum, Jesmin
, p. 1125 - 1129 (2017/03/22)
Diazonium ions were prepared from aromatic amines and immobilized in cation exchange resin support and used for the synthesis of triazenes of piperidine and morpholine in a solid phase synthesis. Immobilization is an excellent technique for the stabilization of diazonium ions and can be preserved in the solid state. Using resin immobilized diazonium ions, triazene synthesis is carried out in the absence of acids thereby increasing the yield of the product and simplifying work up.
Sulfide synthesis through copper-catalyzed C-S bond formation under biomolecule-compatible conditions
Zhang, Yonghong,Li, Yiming,Zhang, Xiaomei,Jiang, Xuefeng
supporting information, p. 941 - 944 (2015/01/09)
We report here an efficient and mild method for constructing C-S bonds. The reactions were carried out with Na2S2O3 as a sulfurating reagent, CuSO4 as a catalyst, and water as solvent without any surfactant. The products were achieved in moderate to excellent yields at room temperature under air. Notably, this reaction is compatible with various biomolecules including amino acids, oligosaccharides, nucleosides, proteins, and cell lysates. This journal is
Synthesis of triazenes by using aryl diazonium silica sulfates under mild conditions
Zarei, Amin,Khazdooz, Leila,Aghaei, Hamidreza,Azizi, Ghobad,Chermahini, Alireza Najafi,Hajipour, Abdol R.
, p. 295 - 302 (2013/11/19)
An efficient, fast and straightforward procedure for the synthesis of aryltriazenes is described in the present paper by using aryl diazonium silica sulfates and secondary amines. Using the present method, different kinds of aryl diazonium silica sulfates
Rhodium(III)-catalyzed C-H activation of arenes using a versatile and removable triazene directing Group
Wang, Chengming,Chen, Hu,Wang, Zhaofeng,Chen, Jiean,Huang, Yong
supporting information; experimental part, p. 7242 - 7245 (2012/09/07)
Diverse opportunities: A Rhodium(III)-catalyzed ortho-selective olefination of arenes using a novel triazene as a directing group is reported. This method exhibits substantial post-functionalization synthetic versatility, overcoming a vital limitation in Ca spa 2-H activation/functionalization products: restricted structural diversity. Copyright
No carrier-added nucleophilic aromatic radiofluorination using solid phase supported arenediazonium sulfonates and 1-(aryldiazenyl)piperazines
Riss, Patrick J.,Kuschel, Sonja,Aigbirhio, Franklin I.
supporting information; experimental part, p. 1717 - 1719 (2012/05/04)
This Letter concerns the investigation of a solid phase based method for no carrier-added nucleophilic [18F]fluorination of aromatic compounds via de-diazofluorination. Initial screening of reaction conditions was conducted using soluble analog
Thermal cis-to-trans isomerisation of triazene dyes in doped polymer films
Tabone, Ryan,Barra, Mónica
experimental part, p. 180 - 186 (2011/01/12)
The kinetics of the thermal conversion of the cis to the trans isomeric forms of 1,3-diphenyltriazene and 1-phenyltriazenes derived from cyclic amines were determined in both poly(methyl methacrylate) and polystyrene doped films in the glassy state, using
Synthesis of Biaryls from Aryltriazenes
Patrick, Timothy B.,Willaredt, Richard P.,DeGonia, David J.
, p. 2232 - 2235 (2007/10/02)
Aryltriazenes react with aromatic solvents in the presence of trifluoroacetic acid to produce biaryls.The mechanism of the reaction involves the formation of arenediazonium trifluoroacetates which lose nitrogen to give mainly aryl radicals.
