Gräßle Simone, Holzhauer Laura, Wippert Nicolai, Fuhr Olaf, Nieger Martin, Jung Nicole, Bräse Stefan
Institute of Biological and Chemical Systems, Karlsruhe Institute of Technology, Kaiserstraße 12, 76131 Karlsruhe, Germany.
Institute of Nanotechnology, Karlsruhe Institute of Technology, Kaiserstraße 12, 76131 Karlsruhe, Germany.
Beilstein J Org Chem. 2024 Jun 20;20:1396-1404. doi: 10.3762/bjoc.20.121. eCollection 2024.
A synthesis route to access triazole-pyrazole hybrids via triazenylpyrazoles was developed. Contrary to existing methods, this route allows the facile -functionalization of the pyrazole before the attachment of the triazole unit via a copper-catalyzed azide-alkyne cycloaddition. The developed methodology was used to synthesize a library of over fifty new multi-substituted pyrazole-triazole hybrids. We also demonstrate a one-pot strategy that renders the isolation of potentially hazardous azides obsolete. In addition, the compatibility of the method with solid-phase synthesis is shown exemplarily.
开发了一种通过三氮烯基吡唑制备三唑-吡唑杂化物的合成路线。与现有方法不同，该路线允许在通过铜催化的叠氮化物-炔烃环加成连接三唑单元之前，对吡唑进行简便的官能化。所开发的方法用于合成五十多种新的多取代吡唑-三唑杂化物库。我们还展示了一种一锅法策略，使潜在危险的叠氮化物的分离不再必要。此外，还示例性地展示了该方法与固相合成的兼容性。
