Domino Reaction of Aromatic Aldehydes and 1,3-Indanediones for Construction of Bicyclo[2.2.2]octanes and Dibenzo[<i>b</i>,<i>g</i>]indeno[1′,2′:3,4]fluoreno[1,2-<i>d</i>]oxonines

Abstract

Triethylamine promoted the pseudo-five-component reaction of aromatic aldehyde with four molecules of 1,3-indanediones in refluxing ethanol to give unique polycyclic bicyclo[2.2.2]octane derivatives containing bridged- and spiro-indanone scaffolds in good yields. The mechanistic studies supported that the reaction included base-catalyzed cyclotrimerization of 1,3-indanedione to give an active cyclic diene and the sequential Diels–Alder reaction with in situ generated 2-arylidene-1,3-indanediones as electron-deficient dienophiles. On the other hand, the pseudo-four-component reaction of salicylaldehyde with 1,3-indanedione afforded the dibenzo[b,g]indeno[1′,2′:3,4]fluoreno[1,2-d]oxonines in high yields. This reaction clearly demonstrated the high efficiency, molecular convergence, atom-economy, and impressive selectivity of multicomponent reactions.