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

Lu Wang, Yin Zhang, An-Qi Miao, Tian-Shu Zhang,* Xiang Wang, Wen-Juan Hao,* Shu-Jiang Tu, Bo Jiang*

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 such as pyrrolo[3,4-c]quinolines, chromeno[3,4-c]pyrroles and benzo[e]isoindoles with moderate to good yields by simple tuning the linkers of 1,7-diynes. This domino protocol demonstrates remarkable compatibility regarding 1,7-diynes with different linkers such as nitrogen and oxygen atoms and hydroxymethyl group and ^tBuONO plays dual roles as a nitro precursor as well as a nitrogen atom source.

Chem. Commun. 2022, 58, 4376–4379; DOI: 10.1039/D2CC00206J