Synthesis of 8-aminoquinoline chelating moieties for chemosensor molecules

Cutler, Alan and Csomos, Attila and Pantl, Orsolya and Dunkel, Petra and Bogdán, Dóra and Steckel, Arnold and Schlosser, Gitta and Mucsi, Zoltán and Kovács, Ervin (2022) Synthesis of 8-aminoquinoline chelating moieties for chemosensor molecules. ARKIVOC, 2022 (3). pp. 41-54. ISSN 1551-7012, ESSN: 1551-7004

Preview

Text Synthesis of 8-aminoquinoline chelating moieties for chemosensor molecules_GK-11746MP published mainmanuscript.pdf Download (725kB) | Preview

Abstract

8-Aminoquinolines are useful molecular motifs for ion sensors. To encourage chemosensor development, new building blocks containing these motifs are essential. 8-Aminoquinoline-2-carbaldehydes are proposed as useful building blocks since their aldehyde group offers the possibility for further transformations. We present a general method for the preparation of these compounds starting from commercially available 8-bromo-2- methylquinoline. Different sidechains for fine-tuning their affinity and selectivity were introduced by a microwave-aided N-arylation using Pd(0) and P-ligands; the desired products were achieved by oxidation. An alternative method is also presented when the product shows high affinity towards the catalyst limiting the effectiveness of the Pd-catalysed the N-arylation.

Actions (login required)

Edit Item