title: Synthesis of Benzo[a]carbazoles and an Indolo[2,3-a]carbazole from 3-Aryltetramic Acids.
abstract: A simple and flexible approach to 3-pyrrolin-2-one fused carbazoles is disclosed. The key step involves the BF3-mediated electrophilic substitution of indoles with N-alkyl-substituted 3-aryltetramic acids, which provides access to indole-substituted 3-pyrrolin-2-ones. Scholl-type oxidative cyclizations of these materials led to the formation of the corresponding 3-pyrrolin-2-one-fused benzo[a]carbazoles and indolo[2,3-a]carbazoles. This work represents the first synthesis of the benzo[a]pyrrolo[3,4-c]carbazol-3(8H)-one ring system, while the indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one ring system is found in a number of biologically active compounds including the protein kinase C (PKC) inhibitor, staurosporine.
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Nathanyal J
authors.initials: NJ
authors.lastname: Truax
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Fernando
authors.initials: F
authors.lastname: Banales Mejia
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Deborah O
authors.initials: DO
authors.lastname: Kwansare
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Megan M
authors.initials: MM
authors.lastname: Lafferty
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Maeve H
authors.initials: MH
authors.lastname: Kean
authors.affiliation: Department of Chemistry, Hobart and William Smith Colleges , Geneva, New York 14456, United States.
authors.forename: Erin T
authors.initials: ET
authors.lastname: Pelkey