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A New and Effective One‐Pot Synthesis of Polysubstituted Carbazoles Starting from β‐Nitro‐β,γ‐Unsaturated‐Ketones and Indoles
Author(s) -
Lupidi Gabriele,
Bassetti Benedetta,
Ballini Roberto,
Petrini Marino,
Palmieri Alessandro
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100342
Subject(s) - chemistry , nitro , intramolecular force , organic chemistry , friedel–crafts reaction , nitrous acid , molecule , combinatorial chemistry , catalysis , alkyl
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%).