jo0c00283_si_002.cif (3.62 MB)

Synthesis of 8‑Alkoxy‑5H‑isochromeno[3,4‑c]isoquinolines and 1‑Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C–H Functionalization of Benzimidates with 4‑Diazoisochroman-3-imines and 4‑Diazoisoquinolin-3-ones

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posted on 2020-03-30, 12:34 authored by Zhenmin Li, Jianwei Xie, Ping Lu, Yanguang Wang
Rh­(III)-catalyzed C–H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno­[3,4-c]­isoquinolines in moderate to excellent yields with a broad range of substrate scope. The reaction was carried out under mild reaction conditions and could be scaled up with practical usage. Similar reaction between benzimidates and 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols in excellent yields. Moreover, the synthesized products could be conveniently transformed to the corresponding heterocycles with a 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures in medicinal chemistry.