Manganese-catalyzed cascade annulations of alkyne-tethered -alkoxyamides: synthesis of polycyclic isoquinolin-1(2)-ones

A strategy for the synthesis of isoxazolidine/1,2-oxazinane-fused isoquinolin-1(2 H )-ones from alkyne-tethered N -alkoxyamides is described, in which cheap Mn(acac) 2 is used as a catalyst to facilitate a radical cascade annulation. The method features mild conditions, additive-free reaction and br...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-12, Vol.17 (48), p.1167-1171
Main Authors: Kong, Gui-Xian, Han, Jiao-Na, Yang, Dandan, Niu, Jun-Long, Song, Mao-Ping
Format: Article
Language:English
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Summary:A strategy for the synthesis of isoxazolidine/1,2-oxazinane-fused isoquinolin-1(2 H )-ones from alkyne-tethered N -alkoxyamides is described, in which cheap Mn(acac) 2 is used as a catalyst to facilitate a radical cascade annulation. The method features mild conditions, additive-free reaction and broad substrate scope. It is the first example via manganese/air catalytic systems to construct isoquinolin-1(2 H )-one heterocycles. Inexpensive Mn( ii )-catalyzed cascade annulations with air as the green oxidant were reported, enabling the facile preparation of isoquinolin-1(2 H )-one scaffolds.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02364j