Divergent synthesis of arylated pyridin-2(1H)-one derivatives via metal-catalysed cross-coupling processes

Siddle, J. S., Batsanov, A. S., Caldwell, S. T. , Cooke, G. and Bryce, M. R. (2010) Divergent synthesis of arylated pyridin-2(1H)-one derivatives via metal-catalysed cross-coupling processes. Tetrahedron, 66(32), pp. 6138-6149. (doi: 10.1016/j.tet.2010.05.108)

Abstract

1,5-Di(hetero)arylated-pyridin-2(1H)-one derivatives have been readily obtained in good yields starting from 2-fluoro-5-pyridylboronic acid. The sequence comprises three steps: (i) palladium-catalysed Suzuki-Miyaura reaction; (ii) base-catalysed hydrolysis; (iii) copper-catalysed C-N coupling. X-ray crystal structures are reported for selected pyridin-2(1H)-one derivatives. These compounds are of interest as new scaffolds for drug discovery. .

• Item Type: Articles
• Keywords: 2-HYDROXYPYRIDINES 2-PYRIDONE ACIDS ANALOGS Arylation Boronic acid C-N coupling Copper catalysis Cross-coupling CUPRIC ACETATE DIMETHYL-SULFOXIDE EFFICIENT EQUILIBRIUM HYDROGEN-BONDS N-ARYLATION Palladium catalysis Pyridine Pyridone Suzuki-Miyaura reaction
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Caldwell, Dr Stuart and Cooke, Professor Graeme
• Authors: Siddle, J. S., Batsanov, A. S., Caldwell, S. T., Cooke, G., and Bryce, M. R.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron
• ISSN: 0040-4020