Nitrative bicyclization of 1,7-diynes for accessing skeletally diverse tricyclic pyrroles

Abstract

A novel metal-free nitrative bicyclization of 1,7-diynes with ^tBuONO in the presence of H₂O is reported, producing three types of skeletally diverse tricyclic pyrroles, namely pyrrolo[3,4-c]quinolines, chromeno[3,4-c]pyrroles and benzo[e]isoindoles, with moderate to good yields by simply tuning the linkers of the 1,7-diynes. This domino protocol demonstrates remarkable compatibility regarding 1,7-diynes with different linkers, such as nitrogen and oxygen atoms and a hydroxymethyl group, and ^tBuONO plays dual roles as a nitro precursor as well as a nitrogen atom source.