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Zur Chemie der vicinalen Triketone, XII Versuche zur Darstellung vonSchiffschen Basen aus cyclischen, vicinalen Triketonen

The chemistry of vicinal triketones, XII. Attempts for preparingSchiff bases from cyclic vicinal triketones

  • Organische Chemie Und Biochemie
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Abstract

The quinolinetrionesTMCH, PCH, MCH and phenalene trione (PT) do not react with aryl isocyanates toSchiff bases5a, but react by ring contraction to yield the spiro-imidazolidines2 a-d,3 a-e,4 a-b and5 a-cbd. However, reaction of ninhydrine with aryl isocyanates gives the 1:2 adductes1 a-e. Benzal aniline reacts withTMCH, PCH. andPT to yield known phenoxazine derivatives2c,11. In contrast,PCH orMCH react with benzylidene benzalaniline to yield theSchiff bases7 a-b. which can be transformed into the “bisamine”8. comparable to the ninhydrine reaction.

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Authors and Affiliations

  1. Institut für Organische Chemie, Karl-Franzens-Universität Graz, A-8010, Graz, Österreich

    Friedrich Günzl & Helga Wittmann

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  1. Friedrich Günzl
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  2. Helga Wittmann
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Herrn emer. o. Univ. Prof. Dr.Erich Ziegler, Graz, mit besten Wünschen zur Vollendung des 70. Lebensjahres gewidmet.

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Günzl, F., Wittmann, H. Zur Chemie der vicinalen Triketone, XII Versuche zur Darstellung vonSchiffschen Basen aus cyclischen, vicinalen Triketonen. Monatsh Chem 113, 1299–1310 (1982). https://doi.org/10.1007/BF00808745

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  • DOI: https://doi.org/10.1007/BF00808745

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