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Thermal and spectroscopic characterization of several derivatives containing a new organic ring system

The tropane-6-spiro-5′-hydantoin structure

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Abstract

Several derivatives containing a new organic ring system, the tropane-6-spiro-5′-hydantoin structure (namely 8-alkyl-8-azabicyclo [3.2.1.] octane-6-spiro-5′-imidazoline-2′,4′-diones) have been characterized by thermal (DSC and simultaneous DTA-TG-DTG) and spectroscopic techniques (IR,1 H-NMR,13 C-NMR). X-ray powder diffraction and elemental analysis were applied for structural and molecular characterization. All the compounds melt in the range 160–250°C and undergo decomposition with progressive mass loss after the solid-liquid thermal transition with molecular degradation. It was found that tropane-6-spiro-5′-hydantoin derivatives with the hydantoin ring in β position are thermally less stable than those containing this ring in α position.

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Authors and Affiliations

  1. Instituto de Ciencia de Materiales, Centro Mixto Consejo Superior de Investigaciones Cientificas (C.S.I.C.), Universidad de Sevilla, c/Américo Vespuccio s/n, Isla de La Cartuja, 41092, Sevilla

    P. J. Sánchez-Soto, A. Ruiz-Conde & M. A. Avilés

  2. Departamento de Química Orgánica y Farmaceůtica, Facultad de Farmacia, Universidad Complutense, 28040, Madrid

    M. Villacampa

  3. Departamento de Farmacia y Tecnología Farmaceútica, Facultad de Farmacia, Universidad de Sevilla, c/Professor García González s/n, 41012, Sevilla, Spain

    J. M. Ginés & M. J. Arias

Authors
  1. P. J. Sánchez-Soto
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  2. M. Villacampa
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  3. J. M. Ginés
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  4. A. Ruiz-Conde
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  5. M. A. Avilés
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  6. M. J. Arias
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Additional information

One of the authors (Dr. M.V.) thanks partial financial support from CICYT through research project PA 86-0317. Thanks are extended to Ms. A. García and Mr. J. C. Rivero for artwork.

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Sánchez-Soto, P.J., Villacampa, M., Ginés, J.M. et al. Thermal and spectroscopic characterization of several derivatives containing a new organic ring system. Journal of Thermal Analysis 50, 665–683 (1997). https://doi.org/10.1007/BF01979038

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  • DOI: https://doi.org/10.1007/BF01979038

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