Abstract:Novel 2,4-dichloro-5-phenylcyclopent-4-ene-1,3-dione and 5-aryl-4-chlorocyclopent-4-ene-1,3-dione were synthesized by the Suzuki–Miyaura or Friedel–Crafts reactions of the di- and trichlorocyclopentenone monoketals and subsequent hydrolysis of the ketal function. Condensation of these diones with (hetero)aromatic aldehydes afforded multifunctional 1,3-cyclopentenediones that showed anticancer activity.Keywords: organochlorine compounds, cyclopentenones, ketals, Suzuki–Miyaura reaction, Friedel–Crafts reaction, Knoevenagel condensation, aldehydes, cross-conjugated cyclopentene-1,3-diones, cytotoxicity.
Citation:
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, A. N. Lobov, D. V. Ishmetova, V. A. Vakhitov, M. S. Miftakhov, “Cytotoxicity of novel cross-conjugated arylated cyclopentene-1,3-diones”, Mendeleev Commun., 32:2 (2022), 183–185
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https://www.mathnet.ru/eng/mendc/v32/i2/p183
This publication is cited in the following 4 articles:
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “Double Acylation Product in the SnCl4-promoted Reaction of 4,5-Dichlorocyclopent-4-en-1,3-dione with 1,3,5-Trimethoxybenzene”, Russ J Org Chem, 59:8 (2023), 1449
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, M. S. Miftakhov, “Double acylation product in the snsl<sub>4</sub>-promoted reaction of 4,5-dichlorocyclopent-4-en-1,3-dione with 1,3,5-trimethoxybenzene”, Žurnal organičeskoj himii, 59:8 (2023), 1096
A. F. Schmidt, A. A. Kurokhtina, E. V. Larina, N. A. Lagoda, S. A. Gurevich, D. A. Yavsin, I. N. Krotova, V. M. Zelikman, T. N. Rostovshchikova, I. G. Tarkhanova, “Advanced heterogeneous Pd catalysts for the Suzuki–Miyaura reaction with aryl bromides”, Mendeleev Commun., 33:2 (2023), 177–179
V. A. Egorov, L. S. Khasanova, F. A. Gimalova, D. V. Ishmetova, M. S. Miftakhov, “Zinc-promoted Reactions of (2Z,E)-[2-Aryl(hetaryl)methylidene]-4-chloro-5-phenyl(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-diones with Methyl Bromoacetate”, Russ J Org Chem, 58:11 (2022), 1668