Synthesis of dibenzo[<i>a</i>,<i>d</i>]cycloheptanoids <i>via</i> aryne insertion into 2-arylidene-1,3-indandiones
作者:Nagaraju Payili、Santhosh Reddy Rekula、Anjaiah Aitha、V. V. S. R. N. Anji Karun Mutha、Challa Gangu Naidu、Satyanarayana Yennam
DOI:10.1039/c9ob01900f
日期:——
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
通过共轭添加氟化物,然后通过正式的CC插入,在2-芳基-1,3-茚满二酮上进行了新颖且出乎意料的芳烃插入级联反应,从而以单一异构体的高收率得到了二苯并[a,d]环庚烷衍生物。该反应代表了在芳烃化学中罕见的环状烯酮CC键插入(酰基-烯基化)的情况。有趣的是,带有富电子官能团的2-亚芳基-1,3-茚满二酮通过[4 + 2]环加成反应然后扩环提供二苯并[a,c]蒽-9,14-二酮衍生物。