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A Mg(OTf)-catalyzed asymmetric Michael addition/cyclization cascade reaction between 3-isothiocyanato oxindoles and 2-arylidene-1,3-indanediones has been developed. This transformation provides an efficient and concise approach to biologically important bispiro[indanedione-oxindole-pyrrolidinyl]s under mild conditions in good to excellent yields (70-99% yields) with moderate to good stereoselectivities (up to 99% and >95:5 d.r.). Notably, biological investigation reveals that one of the synthesized bispiro[indanedione-oxindole-pyrrolidinyl]s exhibits promising cytotoxicity against NCI-H460 human lung cancer and SW-620 human colon cancer cells.
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http://dx.doi.org/10.1021/acs.joc.5c01565 | DOI Listing |
J Org Chem
September 2025
Department of Radiation and Medical Oncology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, P. R. of China.
A Mg(OTf)-catalyzed asymmetric Michael addition/cyclization cascade reaction between 3-isothiocyanato oxindoles and 2-arylidene-1,3-indanediones has been developed. This transformation provides an efficient and concise approach to biologically important bispiro[indanedione-oxindole-pyrrolidinyl]s under mild conditions in good to excellent yields (70-99% yields) with moderate to good stereoselectivities (up to 99% and >95:5 d.r.
View Article and Find Full Text PDFSci Rep
July 2025
Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran.
A simple and highly chemoselective heteroannulation protocol for the synthesis of polysubstituted heterocycles is reported. In this work, various oxa-aza[3.3.
View Article and Find Full Text PDFChemistryOpen
July 2025
Department of Organic Chemistry and Natural Products, Chemistry and Chemical Engineering Research Center of Iran, Tehran, 14968-13151, Iran.
A double aldol condensation-Michael addition-cyclization-double click reaction sequence is conducted in one pot for the synthesis of a novel series of tetrahydro-chromene derivatives anchored with dual triazole rings. The process is optimized primarily step by step under ultrasonic irradiation in a basic aqueous t-BuOH medium. The steps are then successfully combined into a four-component one-pot reaction using the optimum conditions, where the whole operation took less than 2 h to complete.
View Article and Find Full Text PDFACS Omega
July 2025
Department of Chemistry, Federal University of Juiz de Fora, Rua José Lourenço Kelmer, Campus Universitário São Pedro, Juiz de Fora, Minas Gerais 36036-900, Brazil.
A theoretical investigation of the reaction among benzaldehyde, Meldrum's acid, and 6-aminouracil in aqueous solution is presented in this study, incorporating the impact of temperature on both the thermodynamic and kinetic aspects of the reaction. Five free energy profiles are presented, concerning the Knoevenagel condensation, Michael addition, cyclization, propanone, and CO release. We have also performed a simple kinetic analysis and a detailed microkinetic analysis.
View Article and Find Full Text PDFOrg Biomol Chem
June 2025
Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Pune, India-410 008.
The organocatalyzed one-pot Michael addition reaction of propanal to isatylidene malononitriles remains largely unexplored due to challenges in controlling the reaction and preventing side processes such as aldol condensation, self-aldolization, and 1,3-dipolar cycloaddition. In this study, we introduce a one-pot methodology for the synthesis of 3'-alkyl spiro[2-pyran-3,4'-indoline] an organocatalyzed Michael addition of simple propanal to isatylidene malononitrile derivatives, which are generated from isatin derivatives and malononitrile. Subsequent reduction of the Michael adduct with NaBH leads to the target product with high efficiency under mild conditions.
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