A tandem sequence involving palladium-catalyzed sequential Heck-reduction-cyclization transformations in mild conditions has been developed for the synthesis of oxindoles. The protocol involves inexpensive reagents and does not require any additives such as base or ligands.
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http://dx.doi.org/10.1021/jo802467s | DOI Listing |
Org Biomol Chem
January 2025
Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. China.
As one of the main fragments in medical drugs, spirooxindole has received considerable attention from organic and medicinal chemists. In the past few decades, chemists have been searching for more straightforward and efficient methods to produce compounds containing a spirooxindole fragment. In this regard, isatin-derived Morita-Baylis-Hillman (MBH) carbonates have been widely used as versatile building blocks for the synthesis of spirooxindole structures.
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December 2024
Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan.
The chiral amine catalyzed diastereo- and enantioselective [3 + 2] cycloaddition between isatin-derived azomethine ylides and α,β-unsaturated aldehydes was successfully carried out to afford spiro[oxindole-3,2'-pyrrolidine]s. It was anticipated that the formation of azomethine ylides occurred the cycloreversion of dispirooxindole-imidazolidines, which are precursor imine homodimers, in aqueous solvents.
View Article and Find Full Text PDFChemMedChem
December 2024
IICT CSIR: Indian Institute of Chemical Technology, Department of Applied Biology, Hyderabad, INDIA.
An efficient and concise synthesis of highly functionalized bridged coumarins has been developed through a diastereoselective double Michael addition reaction of p-quinols with various 4-hydroxy coumarins under catalyst-free conditions in H2O-DMSO (8:2). The method has been applied to oxindoles for the synthesis of a variety of bridged-oxindoles and bridged-spiroxindoles in presence of a DABCO base using H2O-EtOH (8:2) as solvent medium. The strategy is simple, highly atom economical as there is no by-product and environmentally benign (E-factor = 0.
View Article and Find Full Text PDFSci Rep
December 2024
Department of Chemistry and Mineralogy, Institute of Bioanalytical Chemistry, Leipzig University, Deutscher Platz 5, 04103, Leipzig, Germany.
In this study, we investigated a novel anti-cancer drug design approach by revisiting diclofenac-based carborane-substituted prodrugs. The redesigned compounds combine the robust carborane scaffold with the oxindole framework, resulting in four carborane-derivatized oxindoles and a unique zwitterionic amidine featuring a nido-cluster. We tested the anti-cancer potential of these prodrugs against murine colon adenocarcinoma (MC38), human colorectal carcinoma (HCT116), and human colorectal adenocarcinoma (HT29).
View Article and Find Full Text PDFChem Biodivers
December 2024
Department of Chemistry, Guru Nanak Dev University, Amritsar, India.
A series of 1H-1,2,3-triazole-tethered spirocyclopropyl oxindole-isatin hybrids were synthesized using a copper-promoted click reaction and evaluated for their anti-proliferative activities against triple-negative breast cancer cell lines. The most potent compound in the series outperformed tamoxifen and 5-fluorouracil, with selectivity indices of 1.60 and 1.
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