Easy Access to Fused Tricyclic Quinoline Derivatives through Metal-Free Electrocatalytic [4 + 2] Annulation

An efficient electrocatalytic cycloaddition approach for the construction of a lactone- or lactam-fused quinoline framework is documented. Diverse arrays of functionalities are well-compatible under this metal-free, mild, and scalable electro-redox protocol. Mechanistic studies indicate an iodide-me...

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Veröffentlicht in:ACS Organic & Inorganic Au 2024-10, Vol.4 (5), p.492-497
Hauptverfasser: Ghosh, Sayan, Mallick, Samrat, Karolly, Devika, De Sarkar, Suman
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient electrocatalytic cycloaddition approach for the construction of a lactone- or lactam-fused quinoline framework is documented. Diverse arrays of functionalities are well-compatible under this metal-free, mild, and scalable electro-redox protocol. Mechanistic studies indicate an iodide-mediated electro-oxidation of secondary amines to their corresponding imines and consequent [4 + 2] cycloaddition, fabricating C–C bonds followed by rapid aromatization leading to the six-membered core structure.
ISSN:2694-247X
2694-247X
DOI:10.1021/acsorginorgau.4c00037