Synthesis 2019; 51(20): 3796-3804
DOI: 10.1055/s-0039-1690615
paper
© Georg Thieme Verlag Stuttgart · New York

Molybdenum-Mediated One-Pot Synthesis of Pyrazoles from Isoxazoles

Marine Rey
,
Galapagos SASU, 102 Avenue Gaston Roussel 93230 Romainville, France   eMail: Stephane.Beaumont@glpg.com
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Publikationsverlauf

Received: 23. Juli 2019

Accepted after revision: 02. August 2019

Publikationsdatum:
26. August 2019 (online)


Abstract

A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.

Supporting Information

 
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