Nitrative bicyclization of 1,7-diynes for accessing skeletally diverse tricyclic pyrroles
Lu Wang1, Yin Zhang1, An-Qi Miao1
1School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116, P. R. China. wjhao@jsnu.edu.cn.
Abstract:
A novel metal-free nitrative bicyclization of 1,7-diynes with BuONO 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 BuONO plays dual roles as a nitro precursor as well as a nitrogen atom source.
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