Three-component synthesis of arylsulfonyl-substituted indolo[2,1-a]isoquinolinones and benzimidazo-[2,1-a]isoquinolin-6(5H)-ones by SO2 insertion and radical cascade cyclization

Abstract

An efficient arylsulfonylation/cyclization of 2-aryl-N-methacryloyl indoles with potassium metabisulfite and aryldiazonium tetrafluoroborates was developed. A series of variously substituted arylsulfonyl indolo[2,1-a]isoquinolin-6(5H)-ones were formed in moderate to good yields via utilization of the nature abundant inorganic salt potassium metabisulfite as a SO₂ surrogate. Additionally, this three-component protocol can also be employed for the synthesis of arylsulfonyl-substituted benzimidazo-[2,1-a]isoquinolin-6(5H)-ones.