16978-76-0Relevant articles and documents
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.
1-Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium-ILs, with [BMIM(SO3H)][OTf] or Sc(OTf)3 as Promoter, and Pd(OAc)2 or NiCl2·glyme as Catalyst
Sutar, Suraj M.,Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
supporting information, p. 6088 - 6093 (2019/09/17)
1-Aryltriazenes, the protected and more stable form of aryl-diazonium species, can be conveniently unmasked with Br?nsted acidic-IL or Sc(OTf)3 and coupled with a host of aryl/heteroaryl boronic acids, styrenes, and aryl/alkyl acetylenes in the Suzuki, Heck and Sonogashira reactions in one-pot and in respectable isolated yields, by using palladium or nickel catalyst in readily available imidazolium ILs as solvent, under mild conditions. The scope of these reactions are explored, and the potential for recovery/reuse of the IL solvent is also addressed.
COMPOUND, COMPOSITION COMPRISING THE SAME AND PAINT
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Paragraph 0134; 0136-0137; 0151-0155, (2019/10/29)
Provided are a compound represented by chemical formula 1, a composition comprising the same and a paint comprising the composition. In chemical formula 1, each substituent is the same as defined in the specification. The compound of the present invention, as a low temperature curable initiator, can form radicals at a low temperature, helps low temperature polymerization of an acrylic binder resin and performs low temperature curing, thereby providing a paint used in a low temperature curing type coating process.COPYRIGHT KIPO 2020
Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
Cao, Dawei,Zhang, Yonghong,Liu, Chenjiang,Wang, Bin,Sun, Yadong,Abdukadera, Ablimit,Hu, Haiyan,Liu, Qiang
supporting information, p. 2000 - 2003 (2016/06/01)
An efficient, mild, and metal-free approach to direct diazenylation of N-heterocyclic compounds with aryltriazenes using Br?nsted ionic liquid as a promoter has been developed for the first time. Many N-heterocyclic azo compounds were synthesized in good to excellent yields at room temperature under an open atmosphere. Notably, the promoter 1,3-bis(4-sulfobutyl)-1H-imidazol-3-ium hydrogen sulfate could be conveniently recycled and reused with the same efficacies for at least four cycles.
A general access to organogold(III) complexes by oxidative addition of diazonium salts
Huang, Long,Rominger, Frank,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 6435 - 6438 (2016/06/06)
At room temperature under mild photochemical conditions, namely irradiation with a simple blue light LED, gold(i) chloro complexes of both phosphane and carbene ligands in combination with aryldiazonium salts afford arylgold(iii) complexes. With chelating P,N-ligands cationic six- or five-membered chelate complexes were isolated in the form of salts with weakly coordinating counter anions that were brought in from the diazonium salt. With monodentate P ligands or N-heterocyclic carbene ligands and diazonium chlorides neutral arylgold(iii) dichloro complexes were obtained. The coordination geometry was determined by X-ray crystal structure analyses of representative compounds, a cis arrangement of the aryl and the phosphane ligand at the square planar gold(iii) center is observed.
PREPARATION AND MEDICAL USE OF TRIAZENES
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Page/Page column 23; 24; 25, (2016/01/25)
The present invention relates to a novel method for preparing triazenes. Further, the invention relates to novel triazenes and the use of N2O for preparing a compound comprising a triazene group. Further, the invention relates to the use of the
Synthesis of triazenes with nitrous oxide
Kiefer, Gregor,Riedel, Tina,Dyson, Paul J.,Scopelliti, Rosario,Severin, Kay
, p. 302 - 305 (2015/02/18)
Triazenes are valuable compounds in organic chemistry and numerous applications have been reported. Furthermore, triazenes have been investigated extensively as potential antitumor drugs. Here, we describe a new method for the synthesis of triazenes. The procedure involves a reagent which is rarely used in synthetic organic chemistry: nitrous oxide (N2O, laughing gas ). Nitrous oxide mediates the coupling of lithium amides and organomagnesium compounds while serving as a nitrogen donor. Despite the very inert character of nitrous oxide, the reactions can be performed in solution under mild conditions. A key advantage of the new procedure is the ability to access triazenes with alkynyl and alkenyl substituents. These compounds are difficult to prepare by conventional methods because the required starting materials are unstable. Some of the new alkynyltriazenes were found to display high cytotoxicity in in vitro tests on ovarian and breast cancer cell lines.
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
Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 9513 - 9516 (2014/08/18)
Various sulfonamides have been synthesized from triazenes and sulfur dioxide. In the presence of just a catalytic amount of BF3· OEt2, a series of 1-aryl-triazenes were converted into sulfonyl hydrazines in good to excellent yields. When using CuCl2 as the catalyst, the corresponding sulfonamides can be produced from the 1-aryl triazenes in good yields. This journal is the Partner Organisations 2014.
