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This article presents a metal-free catalytic system for the [4+2] cycloaddition of isoquinoline and maleimide derivatives, enabling the one-step construction of structurally complex bridged polycyclic lactams. This three-component tandem cyclization reaction generates C-N, CO, and C-C bonds, achieving functionalization at the C1, N2, C3, and C4 positions of 3-halogenated isoquinolines. This dearomatization strategy exhibits exceptional chemoselectivity and regioselectivity, operates without transition metals, and offers a high atom and step economy.
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http://dx.doi.org/10.1039/d5cc03128a | DOI Listing |
Org Lett
September 2025
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Presented herein is a protocol for the iron-catalyzed [4 + 1] cycloadditions of -Boc-imines with β-ketosulfoxonum ylides through a succession of nucleophilic additions and intramolecular annulation, giving access to functionalized oxazolidine-2-ones in generally good yields. In contrast to the renown Corey-Chaykovsky reaction via N attack to furnish aziridines, this method afforded oxazolidine-2-ones via an O-nucleophilic attack. Features of this strategy include readily accessible starting materials, sustainable catalyst, post-functionalizations of complex molecules, scalability, and exceptional control over diastereoselectivity.
View Article and Find Full Text PDFNat Prod Bioprospect
September 2025
College of Pharmaceutical Sciences, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei University, Baoding, 071002, People's Republic of China.
Five new heterodimers, chalasoergodimers A-E (1-5), and three known heterodimers (6-8), along with four chaetoglobosin monomers (9-12), were isolated from a marine-derived Chaetomium sp. fungus. The structures of new compounds 1-5 were elucidated by HRESIMS, NMR, chemical calculated C NMR and ECD methods.
View Article and Find Full Text PDFBeilstein J Org Chem
September 2025
Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997, Moscow, Russia.
Thioformylium methylide, which is readily generated from chloromethyl(trimethylsilyl)methyl sulfide by the action of fluoride, is used for the synthesis of spirocyclic derivatives from arylidene-azolones. Four types of the corresponding heterocycles have been studied. A series of 7-thia-3-azaspiro[4.
View Article and Find Full Text PDFJ Org Chem
September 2025
Department of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York 14627, United States.
This report presents the alkynyl -Prins cyclization of Achmatowicz adducts, enabling the synthesis of up to 24 (24) highly functionalized [4.3.1] and [3.
View Article and Find Full Text PDFInorg Chem
September 2025
Department of Chemistry, Panskura Banamali College, Panskura RS, Purba Medinipur, WB 721152, India.
We report the synthesis and characterization of a new Schiff base ligand (HL), derived from 2-picolylamine and 2-hydroxy-3-methoxy-5-methylbenzaldehyde. Its reaction with Ni(NO)·6HO and Ln(NO)·HO (Ln = Gd, Tb, Dy) in the presence of triethylamine affords a carbonato-bridged family of heterobimetallic NiLn complexes: [NiLn(L)(L')(μ-CO)(NO)]·MeOH·HO (). During the complexation reaction, ligand HL undergoes an oxidation, followed by C-C coupling to generate a secondary ligand (HL').
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