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Monatshefte für Chemie / Chemical Monthly

, Volume 117, Issue 2, pp 247–253 | Cite as

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

  • Gottfried Heinisch
  • Wolfgang Holzer
  • Galal A. M. Nawwar
Organische Chemie Und Biochemie

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

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.

Keywords

Reactions with Michael Acceptors 2-Amino-5-cyano-4H-pyrane-3-carboxylic acid derivatives 

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Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Gottfried Heinisch
    • 1
  • Wolfgang Holzer
    • 1
  • Galal A. M. Nawwar
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität WienWienÖsterreich

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