Seven-membered ring scaffolds for drug discovery: access to functionalised azepanes and oxepanes through diazocarbonyl chemistry

Article English OPEN
Nortcliffe, Andrew ; Moody, Christopher J. (2015)

Functionalised azepane and oxepane scaffolds were prepared using diazocarbonyl chemistry and elaborated to show their potential use in library synthesis. Key dicarbonyl containing seven-membered rings were functionalised via diastereoselective Luche reduction of the ketone followed by manipulation of the ester and amine groups. Further scaffolds could be accessed by C-alkylation of the dicarbonyl compounds. In addition, an oxepane containing amino acid could be prepared via a diastereoselective enamine reduction.
  • References (33)
    33 references, page 1 of 4

    Reekie, T. A.; Kavanagh, M. E.; Longworth, M.; Kassiou, M. Synthesis 2013, 3211-3227.

    Taylor, R. D.; MacCoss, M.; Lawson, A. D. G. J. Med. Chem. 2014, 57, 5845- 5859.

    Baldessarini, R. J.; Frankenburg, F. R. N. Engl. J. Med. 1991, 324, 746-754.

    Randall, L. O.; Smith, T. H. J. Pharmacol. Exp. Ther. 1951, 103 , 10-23.

    Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073-2077.

    Yet, L. Chem. Rev. 2000, 100, 2963-3008.

    J.; Samas, B.; Yalamanchi, G.; Noe, M. C. J. Org. Chem. 2011, 76, 1937- 1940.

    Roglans, A.; Marquet, J.; Moreno-MaƱas, M. Synth. Commun. 1992, 22, 1249-1258.

    Zhou, J.; Yeung, Y.-Y. Org. Lett. 2014, 16, 2134-2137.

    (10) Cini, E.; Bifulco, G.; Menchi, G.; Rodriquez, M.; Taddei, M. Eur. J. Org. Chem. 2012, 11, 2133-2141.

  • Metrics
    No metrics available
Share - Bookmark