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Vergleichende Reaktivitätsuntersuchungen am neuen Codimeren aus Malonitril und Cyanessigester an Carbonylverbindungen

Synthesis with nitriles, LI.: Reactivity of the new codimer from malononitrile and cyanoacetate with carbonyl compounds-scope and limitations

Synthesen mit Nitrilen, 51. Mitt.

Abstract

The reactivity of 3-amino-2,4-dicyano-methyl-(1d) and-ethyl-crotonate (1e), resp., a new type of codimer from malononitrile and cyanoacetate, was investigated. Condensation reactions with aromatic aldehydes (2a-g), with heterocyclic aldehydes (2j-l), nitrosobenzenes (3a-c) ando-hydroxybenz-and-naphtaldehydes (4a-f), resp., are described, the differences in reactivity, compared with dimer malononitrile and dimeric forms of cyanoacetate (1a-c) are negligible. Condensation compounds of1a with cycloalkanones (5a-c) are able to cyclise with sulfur to cycloalkanonothieno-pyridines (6a-b), while the cycloalkano-derivatives of1d gave no ring closure.

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Herrn Prof. Dr.O. E. Polansky zum 60. Geburtstag in Erinnerung an gemeinsame Tätigkeiten auf dem Gebiet der Nitrilchemie gewidmet.

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Junek, H., Thierrichter, B. & Wibmer, P. Vergleichende Reaktivitätsuntersuchungen am neuen Codimeren aus Malonitril und Cyanessigester an Carbonylverbindungen. Monatshefte für Chemie 110, 483–492 (1979). https://doi.org/10.1007/BF00911935

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Keywords

  • Carbonyl compounds
  • Condensation
  • Malononitrile-cyanoacetate codimer