Issue 43, 2019

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 a 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.

Graphical abstract: Synthesis of dibenzo[a,d]cycloheptanoids via aryne insertion into 2-arylidene-1,3-indandiones

Supplementary files

Article information

Article type
Paper
Submitted
30 Aug 2019
Accepted
11 Oct 2019
First published
11 Oct 2019

Org. Biomol. Chem., 2019,17, 9442-9446

Synthesis of dibenzo[a,d]cycloheptanoids via aryne insertion into 2-arylidene-1,3-indandiones

N. Payili, S. R. Rekula, A. Aitha, V. V. S. R. N. A. K. Mutha, C. Gangu Naidu and S. Yennam, Org. Biomol. Chem., 2019, 17, 9442 DOI: 10.1039/C9OB01900F

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