The Mannich Reaction of Hydrazones Amenable to Solid Phase Synthesis: A Powerful Tool for Heterocycle Preparation

The Mannich Reaction of Hydrazones Amenable to Solid Phase Synthesis: A Powerful Tool for Heterocycle Preparation

Abstract The Mannich reaction of hydrazones with aldehydes and benzylpiperazine yields functionalised hydrazones, which are efficient azoalkene precursors. When the hydrazonopiperazines are thus heated with various isocyanides in the presence of dibromoethane, 5-aminopyrazoles are cleanly formed. Th...

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Veröffentlicht in:Synlett 2002-02, Vol.2002 (2), p.352-354
Hauptverfasser: Atlan, Valérie, Elkaim, Laurent, Grimaud, Laurence, Jana, Nirmal K., Majee, Adinath
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The Mannich reaction of hydrazones with aldehydes and benzylpiperazine yields functionalised hydrazones, which are efficient azoalkene precursors. When the hydrazonopiperazines are thus heated with various isocyanides in the presence of dibromoethane, 5-aminopyrazoles are cleanly formed. The choice of benzylpiperazine in the Mannich reaction allows a simple extension of this reaction to solid phase chemistry.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2002-19745