1021869-29-3Relevant academic research and scientific papers
Synthesis and preliminary anticancer evaluation of new triazole bisphosphonate-based isoprenoid biosynthesis inhibitors
Legigan, Thibaut,Migianu-Griffoni, Evelyne,Redouane, Mohamed Abdenour,Descamps, Aurélie,Deschamp, Julia,Gager, Olivier,Monteil, Ma?lle,Barbault, Florent,Lecouvey, Marc
, (2021)
The synthesis of a new set of triazole bisphosphonates 8a-d and 9a-d presenting an alkyl or phenyl substituent at the C-4 or C-5 position of the triazole ring is described. These compounds have been evaluated for their antiproliferative activity against M
[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
Wang, Hongwei,Ning, Yongquan,Sivaguru, Paramasivam,Zanoni, Giuseppe,Bi, Xihe
supporting information, p. 1550 - 1554 (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.
METHOD FOR THE PREPARATION OF TRIAZOLE COMPOUNDS
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Paragraph 0125, (2015/03/31)
The present invention relates to a process for preparing 1-[6-(morpholin-4-yl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1H-pyrazol-5-ol (I—enol form) or 2-[6-(morpholin-4-yl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1,2-dihydro-3H-pyrazol-3-one (I—keto form) and sodium 1-[6-(morpholin-4-yl)pyrimidin-4-yl]-4-(1H-1,2,3-triazol-1-yl)-1H-pyrazol-5-olate (II) from 1,2,3-triazole (III), methyl bromoacetate (IV-Me-Br) or ethyl bromoacetate (IV-Et-Br), 4,6-dichloropyrimidine (VIII), morpholine (IX) and hydrazine (XII).
General solution to the synthesis of N-2-substituted 1,2,3-triazoles
Wang, Xiao-Jun,Zhang, Li,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.,Wipf, Peter
scheme or table, p. 4632 - 4635 (2010/12/18)
The regioselective N-alkylation of 1,2,3-triazoles 1 - 6 was studied. Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5- trimethylsilyl-1,2,3-triazoles. These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10 - 15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds.
