Dual Proton/Silver-Catalyzed Serial (5 + 2)-Cycloaddition and Nazarov Cyclization of ( E )-2-Arylidene-3-hydroxyindanones with Conjugated Eneynes: Synthesis of Indanone-Fused Benzo[ cd ]azulenes.
Hai-Tao ZhuChun-Miao LiangTing-Yan LiLin-Yan LiRui-Ling ZhangJun-Na WangRui-Qing QiJia-Min ZhangRuo-Han YangYin-Qi YangAn-Xi ZhouXiaojie JinNi-Ni ZhouPublished in: The Journal of organic chemistry (2023)
A one-pot step-economic tandem process involving (5 + 2)-cycloaddition and Nazarov cyclization reactions has been reported for the facile synthesis of indanone-fused benzo[ cd ]azulenes from ( E )-2-arylidene-3-hydroxyindanones and conjugated eneynes. This highly regio- and stereoselective bisannulation reaction is enabled by dual silver and Brønsted acid catalysis and opens up a new avenue for the construction of important bicyclo[5.3.0]decane skeletons.