A 3-hydro-4-pyridinone compound derived from maltol and dopamine has been prepared using a microwave reactor. The molecular structure of the protonated product was confirmed by single crystal X-ray diffraction. Crystals were obtained from a saturated solution of methanol and belong to the triclinic space group P-1 with unit cell parameters a = 8.3801(11) ?; b = 9.2583(12) ?; c = 11.5671(15) ?; α = 73.566(2)°; β = 84.514(2)°; γ = 66.578(2)°. The asymmetric unit contains two molecules.
References
[1]
Santos, M.A.; Marques, S.M.; Chaves, S. Hydroxypyridinones as “privileged” chelating structures for the design of medicinal drugs. Coord. Chem. Rev. 2012, 256, 240–259, doi:10.1016/j.ccr.2011.08.008.
[2]
Thompson, K.H.; Barta, C.A.; Orvig, C. Metal complexes of maltol and close analogues in medicinal inorganic chemistry. Chem. Soc. Rev. 2006, 35, 545–556.
Philpot, C. Bioinorganic chemistry: getting a grip on iron. Nat. Chem. Biol. 2010, 6, 568–570, doi:10.1038/nchembio.411.
[5]
Xiao, G.; van der Helm, D.; Hider, R.C.; Dobbin, P.S. Structure-stability relationships of 3-hydroxypyridin-4-one complexes. J. Chem. Soc. Dalton Trans. 1992, 22, 3265–3271.
[6]
Nelson, W.O.; Rettig, S.J.; Orvig, C. Aluminum and gallium complexes of 1-ethyl-3-hydroxy-2-methyl-4-pyridinone: a new exoclathrate matrix. Inorg. Chem. 1989, 28, 3153–3157, doi:10.1021/ic00315a016.
[7]
Giesecke, J. The structure of catecholamines. V. The crystal and molecular structure of epinine hydrobromide. Acta Cryst. 1976, B32, 2337–2340.
[8]
SAINT 7.23A; Bruker AXS, Inc.: Madison, WI, USA, 2006.
[9]
SADABS 2008; Bruker AXS, Inc.: Madison, WI, USA, 2008.
[10]
Sheldrick, G.M. A short history of SHELX. Acta Cryst. 2008, A64, 112–122.