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

Gabriele Lupidi
Primo
;
Benedetta Bassetti;Roberto Ballini;Marino Petrini;Alessandro Palmieri
Ultimo
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%).
2021
262
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/453591
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