Divergent Construction of Pyrazoles via Michael Addition of N‑Arylhydrazones to 1,2-Diaza-1,3-dienes

Divergent Construction of Pyrazoles via Michael Addition of N‑Arylhydrazones to 1,2-Diaza-1,3-dienes

The base (NaH)-promoted Michael addition of N-arylhydrazones (AHs) with 1,2-diaza-1,3-dienes (DDs) produces unprecedented β-azohydrazone adducts. Strategically, the use of AHs as acyl anion equivalents (d 1 synthon) and DDs as α-electrophiles (a 2 synthon) of carbonyl compounds open the way to two i...

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Veröffentlicht in:Organic letters 2015-04, Vol.17 (8), p.2014-2017
Hauptverfasser: Mantenuto, Serena, Mantellini, Fabio, Favi, Gianfranco, Attanasi, Orazio A
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Aza Compounds - chemistry
Hydrazones - chemistry
Molecular Structure
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
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Zusammenfassung:The base (NaH)-promoted Michael addition of N-arylhydrazones (AHs) with 1,2-diaza-1,3-dienes (DDs) produces unprecedented β-azohydrazone adducts. Strategically, the use of AHs as acyl anion equivalents (d 1 synthon) and DDs as α-electrophiles (a 2 synthon) of carbonyl compounds open the way to two important classes of pyrazole compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00776