85863-05-4Relevant academic research and scientific papers
[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.
Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling
Zhao, Yiming,Van Nguyen, Huy,Male, Louise,Craven, Philip,Buckley, Benjamin R.,Fossey, John S.
supporting information, p. 4224 - 4241 (2018/10/25)
Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates wer
Synthesis of trifluoromethyl-substituted N-aryl-poly-1,2,3-triazole derivatives
Kumar, A. Sudheer,Kommu, Nagarjuna,Ghule, Vikas D.,Sahoo, Akhila K.
, p. 7917 - 7926 (2014/05/20)
Synthesis, characterization, and physical properties of -CF3 and -NO2 substituted N-aryl-polytriazole derivatives are reported. The molecules are prepared by a reliable Cu-catalyzed [3 + 2]-cycloaddition between -CF3 substituted aryl azides and alkynes followed by a nitration sequence and also the base-promoted nucleophilic displacement of the halo groups by the 1,2,3-triazoles. The compounds are characterized by analytical and spectroscopic methods; the solid state structures of some of the compounds are confirmed by X-ray diffraction techniques. The synthesized materials decompose in the range of 195-308 °C. Most of the -CF3 and -NO2 groups-bearing aryl triazoles exhibit good densities and acceptable detonation characteristics. Some of the fluorine containing polytriazole-bearing compounds showed positive heats of formation. This journal is the Partner Organisations 2014.
