First Copper-Catalyzed Intramolecular Amidation in Substituted 4-Iodopyrazoles Leading to the Synthesis of Pyrazolo[4,3-b]- pyridin-5-ones

An unprecedented copper‐catalyzed intramolecular amidation of substituted 4‐iodopyrazoles generated either via Baylis–Hillman or Horner–Wadsworth–Emmons chemistry for the synthesis of pyrazolo[4,3‐b]pyridine‐5‐ones is described. In addition, the effect of the stereochemistry of the acrylamide on the...

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Veröffentlicht in:Advanced synthesis & catalysis 2009-11, Vol.351 (16), p.2715-2723
Hauptverfasser: Nag, Somnath, Nayak, Maloy, Batra, Sanjay
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Sprache:eng
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Zusammenfassung:An unprecedented copper‐catalyzed intramolecular amidation of substituted 4‐iodopyrazoles generated either via Baylis–Hillman or Horner–Wadsworth–Emmons chemistry for the synthesis of pyrazolo[4,3‐b]pyridine‐5‐ones is described. In addition, the effect of the stereochemistry of the acrylamide on the cross‐coupling reaction has been investigated and it is demonstrated that only the Z‐isomer is favoured to undergo the intramolecular cyclization.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900438