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Beiträge zur Chemie der Pyrrolpigmente, 40. Mitt.: Azafulvene, Schlüsselstellen beim Aufbau von Pyrrolpigmenten? —Eine neue Synthese von verdinoiden und rubinoiden Gallenfarbstoffen

On the chemistry of pyrrole pigments, XL: azafulvenes, key intermediates in pyrrole pigment synthesis?—A new synthesis of verdinoid and rubinoid bile pigments

  • Organic Chemistry and Biochemistry
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Abstract

Substituted azafulvenes were generated by dehydrogenation of 5′-methyl-substituted pyrromethenones withDDQ and characterized by UV- and1H-NMR-spectroscopy. Their electrophilic properties were demonstrated using several quenchers and furthermore they were used for a synthesis of verdinoid bile pigments (which easily can be converted to rubinoid systems by the action of NaBH4) with nearly any desired unsymmetrical alkyl substitution patter: The azafulvene spezies was generated by the action ofDDQ on a 5′-methylpyrromethenone and was quenched by an 5′-unsubstituted pyrromethenone. The resulting rubinoid adduct was dehydrogenated immediatly byDDQ — yields were good to high.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Thomas Schlederer

  2. Institut für Analytische, Organische und Physikalische Chemie, Johannes-Kepler-Universität, A-4040, Linz, Österreich

    Heinz Falk

Authors
  1. Heinz Falk
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  2. Thomas Schlederer
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Additional information

39. Mitt.:Falk, H., Höllbacher, G., Hofer, O., Müller, N., Mh. Chem.112, 391 (1981).

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Falk, H., Schlederer, T. Beiträge zur Chemie der Pyrrolpigmente, 40. Mitt.: Azafulvene, Schlüsselstellen beim Aufbau von Pyrrolpigmenten? —Eine neue Synthese von verdinoiden und rubinoiden Gallenfarbstoffen. Monatshefte für Chemie 112, 501–510 (1981). https://doi.org/10.1007/BF00901829

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  • DOI: https://doi.org/10.1007/BF00901829

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