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Synlett 1996; 1996(7): 667-668
DOI: 10.1055/s-1996-5548
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A General and Expedient Method for the Solid-Phase Synthesis of Structurally Diverse 1-Phenylpyrazolone Derivatives

Lutz F. Tietze* , Adrian Steinmetz
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen (Germany), FAX: Int. 49(0)551 39-9476
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Publication Date:
31 December 2000 (online)

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The dianion of polymer-bound acetoacetate 3 was generated and trapped with various alkylating agents 5 to give the corresponding γ-alkylated β-ketoesters 8 exclusively. Subsequent reaction with phenylhydrazine resulted in cyclization with concomitant cleavage from the polymeric support to afford the 1-phenyl-pyrazolones 10 in high purity and good yield. The ease and generality of this approach is demonstrated by the synthesis of several diverse 1-phenyl-pyrazolones.

Solid-Phase Synthesis - Combinatorial Chemistry - Alkylation - Enolates - Pyrazolones - β-Ketoester