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Solvent-Selective Alkoxy Radical-Induced Oxidative β-Scission of C-C/C-N Bonds in Spiro Adducts under Blue LED
V Rukyanaik1, Srinu Tothadi2, Srinivas Basavoju1
1Department of Chemistry, National Institute of Technology Warangal, Hanamkonda, Telangana 506 004, India.
Abstract:
A green and efficient, catalyst-free, solvent-selective, alkoxy radical-induced oxidative β-cleavage of carbon-carbon (C-C)/carbon-nitrogen (C-N) bonds in spiro[pyrrolo[2,1-a]isoquinoline-1,5'-thiazolidine]-3-carboxylates is reported. The method enables C1/C2 functionalization of the isoquinoline core with a thiazolidine-2,4-dione unit. The reaction proceeds under mild conditions with a broad substrate scope and good functional group tolerance (up to 96% yield), using molecular oxygen and blue LED irradiation (465-470 nm) under additive-free conditions.
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