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Updated: Dec 23, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Assembling the prenylneoflavone system through a Pechmann condensation/Mitsunobu reaction/Claisen
Oleg A Lozinski1,2,3, J Bistodeau2, C Bennetau-Pelissero4
1Taras Shevchenko National University of Kyiv, Kyiv, Ukraine.
Abstract:
The multistep synthesis of a prenylneoflavone through a sequence of the Mitsunobu reaction/Claisen rearrangement/olefin cross-metathesis reaction has been accomplished in 5% yield over six steps starting from commercially available 3-methoxyacetophenone. The sequence is shown to be compatible with a Pechmann condensation which proved to be a robust and cost-effective method for the assembling of the α-pyrone core. The results open doors to a general approach to the prenylneoflavone system starting from phenol and acetophenone derivatives.
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