Electrochemical intramolecular C-H/N-H functionalization for the synthesis of isoxazolidine-fused isoquinolin-1(2)-ones

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 1; pp. 16 - 21
• Main Authors: Zhang, Lin-Bao, Geng, Rui-Sen, Wang, Zi-Chen, Ren, Guang-Yi, Wen, Li-Rong, Li, Ming
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 02.01.2020; Royal Society of Chemistry
• Subjects: Amides; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Electrochemistry; Ethanol; free radicals; Green & Sustainable Science & Technology; Green chemistry; Oxidants; Oxidation; Oxidizing agents; Physical Sciences; Science & Technology; Science & Technology - Other Topics; solvents; DIRECTING GROUP; KETONES; ACTIVATION; N-RADICALS; O BOND; CATALYZED SYNTHESIS; STRATEGY; OXIDATIVE ANNULATION; CLEAVAGE; ISOQUINOLONE SYNTHESIS
• ISSN: 1463-9262; 1463-9270; 1463-9270
• DOI: 10.1039/c9gc03290h

A general and practical protocol for the construction of isoxazolidine-fused isoquinolin-1(2 H )-ones has been described by electrochemical-oxidation-induced intramolecular annulation via amidyl radicals. In an undivided cell, isoquinolinones could be easily generated from various available amides bearing CONHOR groups under metal-free, additive-free and external oxidant-free conditions. Moreover, this transformation proceeded smoothly by using cheap 95% ethanol as the green solvent and could be extended to the gram scale. A general and practical protocol for the construction of isoxazolidine-fused isoquinolin-1(2 H )-ones has been described by electrochemical-oxidation-induced intramolecular annulation via amidyl radicals.