Synthesis of chryseno[1, 2-b]heteroarenes and phenanthro[1, 2-b:8, 7-b']diheteroarenes by an SNAr-anionic cyclization cascade reaction strategy. Issue 52 (24th December 2020)

• Record Type: Journal Article
• Authors: Gilmore, James; Hwang, Daeseong; Crissy, Jack M.; Mercado-Rodríguez, James M.; Katz, Jeffrey L.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 52(2020)
• Publication Date: 2020-12-24
• Subjects: Phenacene -- Heteroarene -- SNAr -- Cascade -- Nucleophilc substitution; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152663
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of [5]heterophenacenes bearing one or two indole, furan, or thiophene rings is described using an SN Ar-anionic cyclization cascade strategy. The convergent reaction sequences furnish chryseno[1, 2- b ]heteroarenes and phenanthro[1, 2- b :8, 7- b' ]diheteroarenes in only four synthetic steps. The heteroaromatic functionality is selected and installed in the final step of the syntheses from common ortho -fluoro-ethynylarene precursors.