Biradicals/zwitterions from enallene-isonitriles. Formal [4 + 1] cycloadditions leading to 11H-indeno[1,2-b]quinoline and related compounds.
[reaction: see text] 1,3-Prototropic rearrangement of the benzannulated enyne-isonitriles to the corresponding enallene-isonitriles followed by cycloaromatization generated the putative quinoline biradicals/zwitterions. A subsequent intramolecular radical-radical coupling or electrophilic aromatic substitution then gave the formal [4 + 1] cycloaddition adducts leading to 11H-indeno[1,2-b]quinoline and related compounds.
Lu
Xiaoling
X
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA.
Petersen
Jeffrey L
JL
Wang
Kung K
KK