Construction of indeno[1,2-a]fluorene via domino reaction of 1,3-indanedione and 3-arylideneindolin-2-ones or chalcones?
Organic & Biomolecular Chemistry Pub Date: 2019-09-21 DOI: 10.1039/C9OB01779H
Abstract
An efficient synthetic protocol for novel indeno[1,2-a]fluorene derivatives was successfully developed by the base promoted domino reaction of 1,3-indanedione with 3-arylideneindolin-2-ones. The domino reaction in different solvents selectively gave carbamato- or amino-substituted indeno[1,2-a]fluorene in satisfactory yields. Additionally, a similar domino reaction of 1,3-indanediones with chalcones also gave polysubstituted indeno[1,2-a]fluorenes in high yields. The reaction mechanism is believed to proceed with base-promoted dimerization of 1,3-indanedione, Michael condensation, annulation, ring-opening of indolin-2-one and aromatization process.
![Graphical abstract: Construction of indeno[1,2-a]fluorene via domino reaction of 1,3-indanedione and 3-arylideneindolin-2-ones or chalcones](http://scimg.chem960.com/usr/1/C9OB01779H.jpg)
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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