Herein, we report a new one-pot synthesis of polysubstituted carbazoles starting from β-nitro-β,γ-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%).
A New and Effective One-Pot Synthesis of Polysubstituted Carbazoles Starting from β-Nitro-β,γ-Unsaturated-Ketones and Indoles
Lupidi, G;Bassetti, B;Ballini, R;Petrini, M;Palmieri, A
2021-01-01
Abstract
Herein, we report a new one-pot synthesis of polysubstituted carbazoles starting from β-nitro-β,γ-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%).File in questo prodotto:
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Asian J. Org. Chem. 2021, 10, 2334–2337.pdf
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