99367-80-3Relevant articles and documents
A New Synthesis of 4,5-Dihydroxy-pyrazoles
Kirschke, Klaus,Schmitz, Ernst
, p. 35 - 44 (2007/10/02)
1-Aryl-pyrazolin-5-ones 1 are converted by Knoevenagel condensation with acetone or by reaction with 2,2-dimethyl-1,3-dioxolane 6 to 1-aryl-4-isopropyliden-pyrazolin-5-ones 2.The compounds 2 are epoxidized by hydrogen peroxide forming the spiro-epoxides 3, which can be cleaved to 4,5-dihydroxy-pyrazoles 4 under acidic conditions. 4-Acetoxy-5-hydroxy-pyrazoles 13 are formed directly, when 3 are cleaved in presence of acetic anhydride.The 3,3',3'-trimethyl-1-(4-nitro-phenyl)-pyrazolin-4-spiro-2'-oxiran-5-one 3b undergoes rearrangement to the 1,3-dioxolopyrazole 12.