4368-68-7Relevant academic research and scientific papers
Direct Pd-catalyzed arylation of 1,2,3-triazoles
Chuprakov, Stepan,Chernyak, Natalia,Dudnik, Alexander S.,Gevorgyan, Vladimir
, p. 2333 - 2336 (2007)
A highly efficient method for the synthesis of multisubstituted 1,2,3-triazoles via a direct Pd-catalyzed C-5 arylation has been developed.
Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles
Taib, Layla A.,Keshavarz, Mosadegh,Parhami, Abolfath
, p. 795 - 815 (2021/12/08)
The synthesis and catalytic activity of three 1,2,3-triazole-based ionic organic–inorganic hybrids as novel water-soluble catalysts for the efficient preparation of spirooxindole derivatives are described. At first, three different 1,2,3-triazoles were prepared by click reaction. Then, these synthesized compounds were reacted with 1,4-butane sultone to generate novel solid 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the next step, the newly synthesized organic zwitterions were treated with an aqueous solution of phosphotungstic acid to give three novel 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstates as targeted organic–inorganic hybrid catalysts. The prepared catalysts were fully characterized using FTIR, 1H and 13C NMR, XRD, elemental analysis (CHNS), ESI–MS, DSC, and TG techniques. The introduced novel SO3H-functionalized ionic hybrid catalysts have a cationic organic triazolium with phosphotungstate anion and are water-soluble with appropriate thermal stability. Their catalytic activity was explored for the synthesis of spirooxindoles via the three‐component reaction of 1,3‐dicarbonyl compounds, barbituric acid, and isatin derivatives. The synthesis of desired spirooxindole products was performed in acceptable times with excellent yields in the presence of low loading amount of the prepared 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstate catalysts (10?mmol%) in water. Some highlighted superiorities of the introduced organic–inorganic hybrids in comparison with most of the previously reported catalysts are as follows: clean and straightforward preparation, novelty of the catalysts, green conditions, ease of recovery, and reusability up to three repeated runs with no significant decrease in the catalytic stability. Graphical abstract: [Figure not available: see fulltext.]
A fascinating click strategy to novel 1,2,3-triazolium based organic-inorganic hybrids for highly accelerated preparation of tetrazolopyrimidines
Keshavarz, Mosadegh,Taib, Layla A.
, (2022/01/03)
Herein, click reaction is used for the preparation of novel organic-inorganic Br?nsted acidic ionic solids (BAISs) as new catalysts for the efficient synthesis of tetrazolopyrimidines. A series of mono and disubstituted-1,2,3-triazoles were synthesized un
Generation, regeneration, and recovery of Cu catalytic system by changing the polarity of electrodes
Ananikov, Valentine P.,Lotsman, Kristina A.,Metlyaeva, Svetlana A.,Rodygin, Konstantin S.,Samoylenko, Dmitriy E.,Seitkalieva, Marina M.
, p. 1132 - 1140 (2022/02/17)
Considering a complete life cycle of metal catalysts, metals are usually mined from ores as salts (MX′n), industrially processed to the bulk metal (M) and then converted into the salts again (MXn) to be used as catalyst precursors. Under catalytic conditions, metal salts undergo transformations to form catalytically active species (MLn), and the anion (X) is typically converted to waste. Thus, there are extra steps before a catalytic process may start, and the chemical transformation involved therein generates considerable amounts of waste. Here, we study the strategy for merging electrodissolution with catalysis to skip these extra steps and demonstrate efficient waste-minimized transformations to access Cu catalysts from the metal. Bulk metal from an electrode can be transformed directly into a catalytic reaction under the action of electric current. As a representative example, dipolar addition of azides to alkynes was successfully catalyzed by copper metal. The reaction was carried out in an ionic liquid (IL), which acted simultaneously as an electrolyte, a solvent and stabilizer of the formed catalytically active species. The used catalyst can be regenerated (or reactivated, if necessary) by application of reverse polarity of electrodes and directly reused again. For metal and solvent recovery, the ILs used were easily separated from copper species by passing an electric current. The applicability of the copper-catalyzed transformation was additionally tested for cross-coupling of thiols with aryl halides (the Ullmann reaction), click reaction with calcium carbide and three-component azide-halide-alkyne coupling. The mechanism of copper dissolution from an electrode was studied, and the intermediates were identified by means of XRD, X-ray and HRESI-MS.
Synthesis, characterization, and antimicrobial activity of lipophilic N,N′-bis-substituted triazolium salts
Fico, Dominic,Gorden, John D.,Johnson, Shanina S.,King, Lauren B.,Lin, Zi Jie,Martz, Luke,Rodriguez, Isabelle,Shelton, Kerri L.,Ta, Thong,Wilson, Julie A.
supporting information, (2021/11/30)
A series of N,N′-bis-substituted triazolium salts have been synthesized using 1H-1,2,4-triazole, 1H-1,2,3-triazole, and 1H-1,2,3-benzotriazole. Synthesized compounds were tested for their antimicrobial activities against a panel of representative ESKAPE p
[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
Bi, Xihe,Ning, Yongquan,Sivaguru, Paramasivam,Wang, Hongwei,Zanoni, Giuseppe
supporting information, (2021/09/30)
1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.
Regioselectivity of the 1,3-Dipolar Cycloaddition of Organic Azides to 7-Heteronorbornadienes. Synthesis of β-Substituted Furans/Pyrroles
Gil De Montes, Enrique,Mart?nez-Bailén, Macarena,Carmona, Ana T.,Robina, Inmaculada,Moreno-Vargas, Antonio J.
, p. 8923 - 8932 (2020/08/14)
An efficient procedure for the preparation of β-substituted furans/pyrroles is presented. The methodology is based on the use of 7-oxa/azanorbornadienes as dipolarophiles in 1,3-dipolar cycloaddition with benzyl azide. The triazoline cycloadduct thus form
Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides
Giel, Marie-Claire,Smedley, Christopher J.,Mackie, Emily R. R.,Guo, Taijie,Dong, Jiajia,Soares da Costa, Tatiana P.,Moses, John E.
, p. 1181 - 1186 (2019/12/11)
The boom in growth of 1,4-disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI-catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click-inspired protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1-substituted-1,2,3-triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts.
An azide and acetylene free synthesis of 1-substituted 1,2,3-triazoles
Patterson, Sarah J.M.,Clark, Peter R.,Williams, Glynn D.,Tomkinson, Nicholas C.O.
supporting information, (2020/10/13)
This paper details a simple and efficient 3-component synthesis of 1-substituted 1,2,3-triazoles using a primary amine, 2,2-dimethoxyacetaldehyde and tosylhydrazide. The reaction proceeds in good to excellent yields using either aliphatic or aromatic amine substrates and is tolerant of a wide range of functional groups including electron-rich and deficient aryl groups, terminal alkynes, ketones and highly sterically encumbered amines.
One-Pot, Metal- And Azide-Free Synthesis of 1,2,3-Triazoles from α-Ketoacetals and Amines
Hawkins, Joel M.,Sutton, Scott C.,Zehnder, Luke R.
supporting information, p. 175 - 178 (2020/01/23)
An efficient one-pot two-step synthesis of 1,4-disubstituted 1,2,3-triazoles from α-ketoacetals and amines is presented. The method does not use metals, azides, or oxidants, and is compatible with a variety of functional groups, including heterocycles, esters, nitriles, and carbamates.
