Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 2168-2179Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02911
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Funding
- National Natural Science Foundation of China [21572196, 21472161]
- Priority Academic Program Development of Jiangsu Higher Education Institutions [BK2013016]
- Top-notch Academic Programs Project of Jiangsu Higher Education Institutions [PPZY2015B112]
- Thousand Talents Plan for Young Professionals of China
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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 spiroindanone 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, atomeconomy, and impressive selectivity of multicomponent reactions.
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