Convenient Synthesis of 11‐Substituted 11H‐Indolo[3, 2‐c]quinolines by Sequential Chemoselective Suzuki Reaction/Double C–N Coupling. Issue 37 (4th October 2017)

• Record Type: Journal Article
• Authors: Pham, Ngo Nghia; Janke, Sophie; Salman, Ghazwan Ali; Dang, Tuan Thanh; Le, Thanh Son; Spannenberg, Anke; Ehlers, Peter; Langer, Peter
• Is Part Of: European journal of organic chemistry. Issue 37(2017)
• Page Start: 5554
• Page End: 5565
• Publication Date: 2017-10-04
• Subjects: Cross‐coupling -- Fused‐ring systems -- Nitrogen heterocycles -- Regioselectivity -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700913
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A pathway to access 11‐substituted 11 H ‐indolo[3, 2‐ c ]quinolines is described. The protocol features a chemoselective Suzuki reaction of o ‐dihaloquinolines with o ‐bromophenylboronic acid, followed by double C–N coupling with primary amines. The molecular structure of a representative product is exemplified, and demonstrates well‐defined π‐stacking interactions in the molecular network. Abstract : Indolo[3, 2 c]quinolones have been prepared by regioselective Suzuki reactions and subsequent double‐Buchwald–Hartwig reactions.