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Synthesis
DOI: 10.1055/a-2681-4862
DOI: 10.1055/a-2681-4862
Paper
FeCl3-Catalyzed Cascade Reactions for Construction of Cyclopentane-Fused Cyclized Spirobicyclized-Indole and Bis(indolyl)methane Scaffolds
Funding Information The authors acknowledge the National Institute of Technology (NIT) Sikkim for infrastructure support. Mr. Ravan Kumar acknowledges fellowship support from the NIT Sikkim.
Abstract
Ferric chloride (FeCl3) catalyzed synthesis of complex scaffolds of cyclopentane-fused cyclized and spirobi[cyclopenta[b]indole] and bis(indolyl)methanes (BIMs) was achieved from acetone and indoles via cascade reactions. Additionally, the formation of tetrahydro-3H-carbazole was observed from 2-methyl-indole. The reaction proceeded through condensation, addition, and intramolecular cyclization reactions. This protocol explored the target-oriented synthesis of three products from the same substrates by varying reaction conditions. This protocol strikingly features sustainable catalysis using mild and earth-abundant metals as catalysts, readily available substrates, and short reaction times, affording a variety of complex indole scaffolds with moderate to good yields. The synthesized products resemble natural and synthetic biologically active compounds containing cyclopenta[b]indole cores, highlighting their biological importance.
Keywords
Indole - Bisindoles - Cascade reactions - Spiro[bicyclopentane] - Cyclopentane - CyclizationPublication History
Received: 07 June 2025
Accepted after revision: 11 August 2025
Article published online:
27 August 2025
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