4368-68-7Relevant articles and documents
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.]
[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.
