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

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.