Reaction of Phenylhydrazine with α,β-Unsaturated Steroidal Ketones: Synthesis of Steroidal Pyrazoles
Reaction of 4-cholesten-6-one (I) with phenylhydrazine in the presence of acetic acid gives 2'-phenyl-4-cholestenopyrazole (V) whereas 6-oxo-4-cholesten-3β-yl acetate (II) and 4-cholestene-3,6-dione (III) afford the same pyrazole, 3-oxo-2'-phenyl-4-cholestenopyrazole (VI). 6β-Bromo-4-cholesten-3-one (IV) gives besides the pyrazole VI, 2'-phenyl-4-cholestenopyrazol-3-one phenylhydrazone (VII) which is also obtained by treating VI with phenylhydrazine.The structures are supported mainly by their spectral behaviour and chemical properties.Probable pathways for their formation have also been suggested.
Ahmad, M. S.,Ansari, Shamim A.,Ali, S. Masarrat
p. 910 - 913
(2007/10/02)
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