PhI(OCOCF3)2‑Mediated
Cyclization of o‑(1-Alkynyl)benzamides: Metal-Free
Synthesis of 3‑Hydroxy-2,3-dihydroisoquinoline-1,4-dione

Yang, Chao; Zhang, Xiang; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang

doi:10.1021/acs.joc.5b00576.s001

jo5b00576_si_001.pdf (4.92 MB)

PhI(OCOCF₃)₂‑Mediated Cyclization of o‑(1-Alkynyl)benzamides: Metal-Free Synthesis of 3‑Hydroxy-2,3-dihydroisoquinoline-1,4-dione

journal contribution

posted on 2015-05-15, 00:00 authored by Chao Yang, Xiang Zhang, Daisy Zhang-Negrerie, Yunfei Du, Kang Zhao

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 o-(1-alkynyl)benzamides in MeCN/H₂O, mediated by metal-free, hypervalent reagent of PhI(OCOCF₃)₂, followed by an oxidative hydroxylation reaction. The mechanism consisting of two pathways has been proposed and discussed.