Abstract
When synthesizing cyclohexane-annulated pyrazolones from a cyclohexonedicarboxylate derivative with phenylhydrazine under the catalysis of sulfuric acid in the air, up to five products were finally obtained from the one-pot procedure. Among the obtained five products derived from the reaction, two unexpected products were identified, an interesting cyclohexane-annulated pyrazolone bearing a hydroperoxide group and a cyclohexene-annulated pyrazolone, both by crystallographic analysis. Reaction optimization and product distributions were investigated in different reaction conditions. A reaction mechanism for the formation of the five products has been proposed, and the two unexpected pyrazolones were suggested to be from the three-step cascade products of the condensation/amidation/peroxidation and the condensation/amidation/dehydration, respectively.
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This work was supported by the National Natural Science Foundation of China (Grant Number 51872140).
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Chen, CY., Qiao, Y., Zhang, L. et al. A detailed investigation into the one-pot cascade reaction of ethyl 3,9-dimethyl-7-phenyl-6H-dibenzo-[b,d]pyran-6-one-8-carboxylate with phenylhydrazine. Res Chem Intermed 46, 4079–4089 (2020). https://doi.org/10.1007/s11164-020-04192-x
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DOI: https://doi.org/10.1007/s11164-020-04192-x