Synthesis of 2-Alkenylpyrazol-3(2H)-one Derivatives Under Mild Conditions
The title compounds have been synthesized by a one-pot two-stage reaction of PCl3, ketone methylhydrazones and methyl acetoacetate.Both stages were carried out at room temperature and the corresponding 2-alkenyl-1,5-dimethylpyrazol-3(2H)-ones 5, which are an unknown series of pyrazolones, were obtained in good yields.Use of a variety of enolizable ketones has shown that the reaction always occurs with the predominance of the (E)-isomer.X-Ray structure determinations of an (E)- and a (Z)-derivative permitted the assignment of their structures.The aromaticity of these derivatives is discussed.
Baccolini, Graziano,Evangelisti, Daniele,Rizzoli, Corrado,Sgarabotto, Paolo
p. 1729 - 1734
(2007/10/02)
The Reaction of Ketone Alkylhydrazones with Phosphorus Trichloride and Methyl Acetoacetate: A Mild New Route to 2-Alkenylpyrazol-3(2H)-one Derivatives
The title compounds have been synthesized by the one-pot reaction at room temperature of ketone alkylhydrazones, PCl3 and methyl acetoacetate; a single crystal X-ray structure determination of the minor isomer of one derivative permitted the assignment of its structure and showed the Z-configuration of the alkenyl group.
Baccolini, Graziano,Sgarabotto, Paolo
p. 34 - 35
(2007/10/02)
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