Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 9, Pages 2334-2337Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100342
Keywords
Carbazoles; Cyclization; Friedel-Crafts reaction; Heterocycles; Nitroolefins
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Funding
- MIUR [2017A5HXFC]
- University of Camerino
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A new one-pot synthesis of polysubstituted carbazoles starting from beta-nitro-beta,gamma-unsaturated-ketones and indoles was reported. The process involved a Friedel-Crafts reaction of indoles to nitroolefins supported by 2,2,2-trifluoroethanol (TFE) followed by an acidic-promoted and microwave-assisted intramolecular cyclization, resulting in products with satisfactory to good overall yields (55-78%).
Herein, we report a new one-pot synthesis of polysubstituted carbazoles starting from beta-nitro-beta,gamma-unsaturated-ketones and indoles. The process is based on a Friedel-Crafts reaction of indoles to nitroolefins supported by 2,2,2-trifluoroethanol (TFE) followed by an acidic-promoted and microwave-assisted intramolecular cyclization, that involves the elimination of both nitrous acid and water molecules. Products were obtained in satisfactory to good overall yields (55-78%).
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