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[4 + 1] Annulation of in situgenerated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
- Source :
- Chinese Chemical Letters; 20210101, Issue: Preprints
- Publication Year :
- 2021
-
Abstract
- 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 situfrom 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.
Details
- Language :
- English
- ISSN :
- 10018417
- Issue :
- Preprints
- Database :
- Supplemental Index
- Journal :
- Chinese Chemical Letters
- Publication Type :
- Periodical
- Accession number :
- ejs57706921
- Full Text :
- https://doi.org/10.1016/j.cclet.2021.09.008