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Synlett 1998; 1998(3): 249-250
DOI: 10.1055/s-1998-1638
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Rare Earth Triflate-Catalyzed Addition Reactions of Acylhydrazones with Silyl Enolates. A Facile Synthesis of Pyrazolone Derivatives

Hidekazu Oyamada* , Shu Kobayashi
  • *Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Japan, and CREST, Japan Science and Technology Corporation (JST), Kagurazaka, Shinjuku-ku, Tokyo 162, Japan; Fax +81 (3) 32 60 47 26
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Publication Date:
31 December 2000 (online)

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In the presence of a catalytic amount of a rare earth triflate, benzoylhydrazones reacted with silyl enolates to afford the corresponding β-N′-benzoylhydrazino esters in high yields. The hydrazino esters thus obtained were readily converted to pyrazolone derivatives by treatment with a base. A three-component reaction between an aldehyde, an acylhydrazine, and a silyl enolate was also performed successfully.

rare earth triflate - hydrazone - ketene silyl acetal - catalytic reaction - pyrazolidinone - Lewis acid catalysis

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