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PhI(OCOCF<sub>3</sub>)<sub>2</sub>‑Mediated Cyclization of <i>o</i>‑(1-Alkynyl)benzamides: Metal-Free Synthesis of 3‑Hydroxy-2,3-dihydroisoquinoline-1,4-dione

By Chao Yang (174810), Xiang Zhang (19800), Daisy Zhang-Negrerie (1490686), Yunfei Du (1490683) and Kang Zhao (407195)


The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of <i>o</i>-(1-alkynyl)­benzamides in MeCN/H<sub>2</sub>O, mediated by metal-free, hypervalent reagent of PhI­(OCOCF<sub>3</sub>)<sub>2</sub>, followed by an oxidative hydroxylation reaction. The mechanism consisting of two pathways has been proposed and discussed

Topics: Biophysics, Biochemistry, Medicine, Cell Biology, Molecular Biology, Neuroscience, Physiology, Cancer, Mental Health, Infectious Diseases, Computational Biology, Chemical Sciences not elsewhere classified, PhI, Cyclization, MeCN, Hydroxy, mechanism, pathway, synthesis, intramolecular cyclization, hypervalent reagent, oxidative hydroxylation reaction, Synthesi, undocumented skeleton
Year: 2015
DOI identifier: 10.1021/acs.joc.5b00576.s001
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Provided by: FigShare
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