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Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Thiophenen

On the reaction behaviour of β-oxo carbonic acid derivatives of the anthracene series in thiophene synthesis

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Summary

β-Oxo-1-anthracenepropionate (3) reacts step by step with phenylisothiocyanate and α-CH-acidic halo compounds to keten-S,N-acetals4, followed by cyclocondensation to give the 4-(1-anthracenyl)-thiophene-3-carboxylates5. In contrast, the reaction of β-oxo-9-anthracenepropionate (6) with isothiocyanates and α-CH-acidic halo compounds yields 5-acyl-2-amino-3-(9-anthracenoyl)-4-hydroxy-thiophenes8. This is caused by the sterical hindrance of the keto group of the anthracene in position 9; thus, the cyclocondensation proceedsvia reaction of the ester group of the β-oxo-propionate. In the same way, 9-acetylanthracene reacts with phenylisothiocyanate and α-CH-acidic compounds to keten-S,N-acetals10 and, in an additional step, to 2-anilino-3-(9-anthracenoyl)-thiophenes11 and 2-(9-anthracenoyl)-methylene-3,4-diphenyl-2,3-dihydro-(1,3)-thiazole12, respectively. The structure of all new compounds was determinated by 2D NOESY NMR spectroscopy.

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Literatur

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    Knieß A(1994) Dissertation, Technische Universität Dresden

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    Augustin M, Rudorf W-D, Schmidt U (1976) Tetrahedron32: 3055

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    Rudorf W-D (1979) Z Chem.19: 100

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Herrn Prof. Dr. habil.G. Großmann zum 65. Geburtstag gewidmet

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Knieß, A., Gruner, M. & Mayer, R. Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Thiophenen. Monatsh Chem 127, 1173–1187 (1996). https://doi.org/10.1007/BF00844693

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Keywords

  • Acetyl anthracenes
  • 2D NOESY NMR of anthracenes
  • β-Oxo-anthracenepropionate
  • β-Oxo-dicarbonyl-compounds
  • Thiophenes