Synthesis of bis-8-hydroxyquinolines via an imination or a Suzuki-Miyaura coupling approach

• Published in: Tetrahedron letters Vol. 58; no. 40; pp. 3803 - 3807
• Main Authors: De Vreese, Rob, Muylaert, Koen, Maton, Cedric, Dereu, Lise, Taillieu, Frederique, Harth, Thomas, Van Deun, Rik, Vrielinck, Henk, Stevens, Christian V., D'hooghe, Matthias
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.10.2017; Elsevier
• Subjects: 8-Hydroxyquinoline; Chemistry; Chemistry, Organic; EPR; Imination; NMR; Physical Sciences; Science & Technology; Suzuki-Miyaura coupling; 8-Hydroxyquinoline; Imination; NMR; Suzuki-Miyaura coupling; EPR; NONLINEAR-OPTICAL PROPERTIES; COMPLEXES; COORDINATION POLYMERS; DERIVATIVES
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.08.039

[Display omitted] •Bis-8-hydroxyquinolines concern underexplored ligands for the preparation of coordination polymers.•Few reports on the synthesis of bis-8-hydroxyquinolines are available.•This work discloses the preparation of bis-8-hydroxyquinolines (via imination or Suzuki-Miyaura coupling) and their analysis. Bis-8-hydroxyquinolines represent an important yet underexplored class of potential ligands for the preparation of various coordination polymers, which can be used in a plethora of applications. In this work, the synthesis of two types of bis-8-hydroxyquinolines, prepared via either an imination or a Suzuki-Miyaura coupling approach, as well as their analysis is discussed. Imination was pursued through the condensation of quinolinecarbaldehydes with diamines or aminoquinolines with dialdehydes, and the Suzuki-Miyaura coupling reactions were evaluated using a bromoquinoline substrate and diboronic acids.