- Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions
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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.
- Davis, Garrett J.,Townsend, Julia A.,Morrow, Madeline G.,Hamie, Mohamed,Shepard, Abigail J.,Hsieh, Chih-Chieh,Marty, Michael T.,Jewett, John C.
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p. 2432 - 2438
(2021/11/18)
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- Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes
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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.
- Schotten, Christiane,Leprevost, Samy K.,Yong, Low Ming,Hughes, Colan E.,Harris, Kenneth D. M.,Browne, Duncan L.
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supporting information
p. 2336 - 2341
(2020/06/05)
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- 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
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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.
- Sutar, Suraj M.,Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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supporting information
p. 6088 - 6093
(2019/09/17)
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- COMPOUND, COMPOSITION COMPRISING THE SAME AND PAINT
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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
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Paragraph 0134; 0136-0137; 0151-0155
(2019/10/29)
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- Ionic Liquid Promoted Diazenylation of N-Heterocyclic Compounds with Aryltriazenes under Mild Conditions
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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.
- Cao, Dawei,Zhang, Yonghong,Liu, Chenjiang,Wang, Bin,Sun, Yadong,Abdukadera, Ablimit,Hu, Haiyan,Liu, Qiang
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supporting information
p. 2000 - 2003
(2016/06/01)
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- A general access to organogold(III) complexes by oxidative addition of diazonium salts
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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.
- Huang, Long,Rominger, Frank,Rudolph, Matthias,Hashmi, A. Stephen K.
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supporting information
p. 6435 - 6438
(2016/06/06)
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- PREPARATION AND MEDICAL USE OF TRIAZENES
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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
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Page/Page column 23; 24; 25
(2016/01/25)
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- Synthesis of triazenes with nitrous oxide
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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.
- Kiefer, Gregor,Riedel, Tina,Dyson, Paul J.,Scopelliti, Rosario,Severin, Kay
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p. 302 - 305
(2015/02/18)
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- Catalytic conversion of aryl triazenes into aryl sulfonamides using sulfur dioxide as the sulfonyl source
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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.
- Li, Wanfang,Beller, Matthias,Wu, Xiao-Feng
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supporting information
p. 9513 - 9516
(2014/08/18)
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- Synthesis of triazenes by using aryl diazonium silica sulfates under mild conditions
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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
- Zarei, Amin,Khazdooz, Leila,Aghaei, Hamidreza,Azizi, Ghobad,Chermahini, Alireza Najafi,Hajipour, Abdol R.
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p. 295 - 302
(2013/11/19)
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- Rhodium(III)-catalyzed C-H activation of arenes using a versatile and removable triazene directing Group
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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
- Wang, Chengming,Chen, Hu,Wang, Zhaofeng,Chen, Jiean,Huang, Yong
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supporting information; experimental part
p. 7242 - 7245
(2012/09/07)
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- Effect of medium on acid-catalyzed decomposition of N-(phenylazo)-substituted nitrogen heterocycles
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Four N-(phenylazo)-substituted saturated nitrogen heterocyclics were synthesized and their structure was confirmed by 1H and 13C NMR spectroscopy. The kinetics of their acid-catalyzed decomposition were studied at various concentrations of the catalyst (pivalic acid) in 40, 30, and 20% (v/v) aqueous ethanol at 25 °C. The values obtained for the observed rate constants were processed by the non-linear regression method according to the suggested kinetic models and by the method of principal component analysis (PCA). The interpretation of the results has shown that the acid-catalyzed decomposition of the heterocyclics under the conditions used proceeds by the mechanism of general acid catalysis, the proton being the dominant catalyst particle of the rate-limiting step. The decrease in the observed rate constant at higher concentrations of the catalyst was explained by the formation of a non-reactive complex composed of the undissociated acid and the respective N-(phenylazo)hetcrocycle. The effect of medium and steric effect of the heterocyclic moiety on the values of catalytic rate constant are discussed.
- Ludwig, Miroslav,Bednarova, Iva,Parik, Patrik
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p. 1654 - 1672
(2007/10/03)
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- Triazenes: A useful protecting strategy for sensitive secondary amines
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The application of aryl triazene as a protecting group for sensitive secondary amines such as 4-piperidone (2) is described. The triazene protected amine is compatible with oxidative and reductive conditions as well as with lithiating and alkylating reagents. The free amine is regenerated by treatment with trifluoroacetic acid.
- Lazny, Ryszard,Poplawski, Janusz,K?bberling, Johannes,Enders, Dieter,Br?se, Stefan
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p. 1304 - 1306
(2007/10/03)
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- Synthesis of Biaryls from Aryltriazenes
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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.
- Patrick, Timothy B.,Willaredt, Richard P.,DeGonia, David J.
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p. 2232 - 2235
(2007/10/02)
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