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Synthesis 2025; 57(02): 397-406
DOI: 10.1055/a-2395-5433
DOI: 10.1055/a-2395-5433
paper
Special Topic Dedicated to Prof. H. Ila
A Regioselective Domino Benzannulation Route to Indeno[1,2-a]fluorene-7,12-diones
We are grateful to CSIR, and to the Science and Engineering Research Board (SERB), India, for financial support (CRG/2022/004763).
Abstract
A base-promoted domino benzannulation reaction of 2,3-dibromoindenone with acyclic 1,3-dicarbonyls resulted in an efficient synthetic protocol for a series of novel polycyclic indeno[1,2-a]fluorenes. The reaction proceeds via the two sequential addition-elimination reactions of nucleophilic species generated from the 1,3-dicarbonyls under basic conditions, serendipitously leading to the benzannulation with two molecules of 2,3-dibromoindenone. The second addition-elimination occurs on the initially formed adduct of 1,3-dicarbonyl with 2,3-dibromoindenone, setting the stage for further intramolecular cyclization and aromatization. Interestingly, unsymmetrical 1,3-dicarbonyls furnished a single regioisomer. The origin of the regioselectivity and plausible mechanism is discussed.
Key word
2,3-dibromoindenone - indeno[1,2-a]fluorene - domino reaction - benzannulation - addition-elimination reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2395-5433.
- Supporting Information
Publication History
Received: 09 June 2024
Accepted after revision: 20 August 2024
Accepted Manuscript online:
20 August 2024
Article published online:
23 September 2024
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