Abstract:
Fluorine-containing analogues of non-steroidal antiinflammatory drugs Tribuzone and Ketazone have been synthesized by reaction of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 3- and 2-oxo esters. Ethyl 3-(pyrazolidin-4-yl)-3-(polyfluoroalkyl)prop-2-enoates have been obtained as Knoevenagel reaction products from 3-oxo esters in the presence of l-proline. Unlike with 3-oxo esters, addition of ethyl 3,3,3-trifluoro-2-oxopropanoate under basic conditions afforded ethyl 2-(pyrazolidin-4-yl)-3,3,3-trifluoro-2-hydroxypropanoate or its salt without elimination of a water molecule.
Citation:
O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, “Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters”, Mendeleev Commun., 30:5 (2020), 630–632
Linking options:
https://www.mathnet.ru/eng/mendc1275
https://www.mathnet.ru/eng/mendc/v30/i5/p630
This publication is cited in the following 2 articles:
L. S. Lapshin, E. V. Shchegolkov, Ya. V. Burgart, G. A. Triandafilova, O. P. Krasnykh, K. O. Malysheva, V. I. Saloutin, “Synthesis of new analgesics based on 4-isopropyl-1-phenyl-3-(trifluoromethyl)pyrazol-5-one”, Mendeleev Commun., 33:2 (2023), 194–196
Ying Liu, Yiping Zhang, Yingkai Zhou, Min Zhang, Hongmei Deng, Liping Song, “Concise One-Pot Multicomponent Reaction Approach to Monofluorinated Spiro-pyrazole-pyridine Derivatives without Additional Catalyst”, SynOpen, 06:03 (2022), 164
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