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 Zhu; Chun-Miao Liang; Ting-Yan Li; Lin-Yan Li; Rui-Ling Zhang; Jun-Na Wang; Rui-Qing Qi; Jia-Min Zhang; Ruo-Han Yang; Yin-Qi Yang; An-Xi Zhou; Xiaojie Jin; Ni-Ni Zhou

doi:10.1021/acs.joc.2c02247

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

J Org Chem. 2023 Mar 17;88(6):3409-3423. doi: 10.1021/acs.joc.2c02247. Epub 2023 Feb 27.

Authors

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji 721013, China.
² Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, Shangrao Normal University, Shangrao 334000, China.
³ Gansu University Key Laboratory for Molecular Medicine & Chinese Medicine Prevention and Treatment of Major Diseases, Gansu University of Chinese Medicine, Lanzhou 730000, China.

PMID: 36847758
DOI: 10.1021/acs.joc.2c02247

Abstract

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.