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Synthesis of Dibenzo[a,d]cycloheptanoids via Aryne Insertion into 2-Arylidene-1,3-indandiones

Abstract

A novel and unexpected aryne insertion cascade reaction on 2-arylidene-1,3-indandiones via conjugate addition of fluoride followed by formal C−C insertion is developed to afford dibenzo[a,d]cycloheptanoid derivatives in good yields with single isomer. This reaction represents a rare instance of cyclic enone C-C bond insertion (Acyl-Alkenylation) in aryne chemistry. Interestingly, 2-arylidene-1,3-indandiones bearing electron rich functional groups provided dibenz[a,c]anthracene-9,14-dione derivatives via [4 + 2] cycloaddition followed by ring expansion.

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Publication details

The article was received on 30 Aug 2019, accepted on 11 Oct 2019 and first published on 11 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01900F
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Synthesis of Dibenzo[a,d]cycloheptanoids via Aryne Insertion into 2-Arylidene-1,3-indandiones

    S. Yennam, N. Payili, R. S. Reddy, A. Aitha, A. K. Mutha and G. N. Challa, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB01900F

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