Iodine-Catalyzed Annulation Reaction of Ortho -Formylarylketones with Indoles: A General Strategy for the Synthesis of Indolylbenzo[ b ]carbazoles.

Autor: Suresh S; Department of Chemistry, National Taiwan Normal University, No. 88, Sec. 4, Ting-Zhou Road, Taipei 11677, Taiwan, Taiwan, R.O.C., Kavala V; Department of Chemistry, National Taiwan Normal University, No. 88, Sec. 4, Ting-Zhou Road, Taipei 11677, Taiwan, Taiwan, R.O.C., Yao CF; Department of Chemistry, National Taiwan Normal University, No. 88, Sec. 4, Ting-Zhou Road, Taipei 11677, Taiwan, Taiwan, R.O.C.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Mar 17; Vol. 88 (6), pp. 3666-3677. Date of Electronic Publication: 2023 Mar 08.
DOI: 10.1021/acs.joc.2c02868
Abstrakt: The iodine-catalyzed cascade reaction of ortho -formylarylketones with indoles for the synthesis of indolylbenzo[ b ]carbazoles is reported. The reaction is initiated in the presence of iodine by two successive nucleophilic additions of indoles with an aldehyde group of ortho -formylarylketones, and the ketone does not undergo a nucleophilic addition and only involves in the Friedel-Crafts-type cyclization. A variety of substrates are tested, and the efficiency of this reaction is demonstrated with gram-scale reactions.
Databáze: MEDLINE