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Synthesis and Structures of New Enaminones

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Abstract

Two isomeric enaminones were obtained by reaction of ethyl 2-hydroxy-4-(4-hydroxy-6-methyl2H-pyran-2-on-3-yl)-4-oxo-2-butenoate (1) and amines (aniline, benzylamine, butylamine and tyramine) in ethanol. The structures of isomers were studied by 13C and 1H NMR spectra, whereas in the case of isomers 2b, 3a, and 4a (Scheme 1), the crystal structures have been determined by single crystal X-ray diffractometry. The compounds 2b and 3a exist in the solid state as N–C=C–C=O, whereas 4a is in the N–C=C–C–OH tautomeric form (Scheme 2, form A and B, respectively). All three structures exhibit very short intramolecular hydrogen bonds of O–H···O [in the range 2.396(3) − 2.448(3) Å] and N–H···O [in the range 2.580(5) − 2.679(3) Å] type, that are reinforced by delocalization. The crystal structures are in addition stabilized by C–H···O weak hydrogen bonds. In 2b and 3a, the discrete dimers are formed by eight-membered ring containing hydrogen bonds; in 4a, the infinite chains along [1 0 1] direction are formed.

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Authors and Affiliations

  1. Department of Chemistry, Veterinary Faculty, University of Zagreb, Heinzlova 55, 10000, Zagreb, Croatia

    Ana Brbot-Šaranović

  2. Laboratory of General and Inorganic Chemistry, Chemistry Department, Faculty of Science, University of Zagreb, PO Box 153, 10001, Zagreb, Croatia

    Gordana Pavlović & Marina Cindrić

Authors
  1. Ana Brbot-Šaranović
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  2. Gordana Pavlović
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  3. Marina Cindrić
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Brbot-Šaranović, A., Pavlović, G. & Cindrić, M. Synthesis and Structures of New Enaminones. Structural Chemistry 11, 65–76 (2000). https://doi.org/10.1023/A:1009224507725

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