Journal of the Chemical Society. Perkin transactions I p. 1729 - 1734 (1992)
Update date:2022-08-02
Topics:
Baccolini, Graziano
Evangelisti, Daniele
Rizzoli, Corrado
Sgarabotto, Paolo
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 <(E)-5c*HCl and (Z)-5b> permitted the assignment of their structures.The aromaticity of these derivatives is discussed.
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