Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

Abstract

A synthesis route to access triazole–pyrazole hybrids via triazenylpyrazoles was developed. Contrary to existing methods, this route allows the facile N-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.

Keywords

• azide
• click reaction
• cuaac
• pyrazole
• triazene
• triazole