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Zur Reaktivität 4,5-ungesättigter 3-Oxoalkannitrile gegenüberMichael-Acceptoren

Reactions of 4,5-unsaturated 3-oxoalkanenitriles withMichael acceptors

  • Organische Chemie Und Biochemie
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Abstract

The 3-oxonitrile1 as well as the 2-benzylidene-3-oxonitrile4 on reaction with benzylidenemalononitrile or malononitrile, respectively, afford 2-amino-4H-pyran derivative3 in high yield. In contrast, reactions of1 and4 with ethyl benzylidenecyanoacetate (6) or ethylcyanoacetate, respectively, predominantly lead to a carbocyclic compound, which is also obtained as main product on attempted condensation of1 with benzaldehyde. Based on spectroscopic data, structure5 is proposed for the novel compound; its formation is interpreted in terms of piperidine-catalysed addition of1 to4 and subsequent intramolecularMichael addition. Reaction mechanisms for the conversion of1 and6 or4 and ethylcyanoacetate to5 are discussed.

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Authors and Affiliations

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

    Gottfried Heinisch, Wolfgang Holzer & Galal A. M. Nawwar

Authors
  1. Gottfried Heinisch
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  2. Wolfgang Holzer
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  3. Galal A. M. Nawwar
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Herrn Univ. Prof. Dr. Dr. h c.K. Kratzl zum 70. Geburtstag gewidmet.

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Heinisch, G., Holzer, W. & Nawwar, G.A.M. Zur Reaktivität 4,5-ungesättigter 3-Oxoalkannitrile gegenüberMichael-Acceptoren. Monatsh Chem 117, 247–253 (1986). https://doi.org/10.1007/BF00809444

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  • DOI: https://doi.org/10.1007/BF00809444

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