Synthesen mit Nitrilen, LVII [1]. Zur Reaktivität von Aminomethylen-malonsäuredinitrilen gegenüber Aldehyden und Orthoestern / Syntheses with Nitriles, LVII [1]. The Reactivity of Aminomethylene-malononitriles with Aldehydes and Orthoesters
Open Access
- 1 November 1979
- journal article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 34 (11) , 1580-1586
- https://doi.org/10.1515/znb-1979-1120
Abstract
Condensation of aminomethy lene-malononitrile (1a) with aromatic aldehydes and dimethylformamide-dimethylacetal, resp., leads to benzylidene-malononitriles (2a, b) and to dimethylaminomethylene-malononitrile (2e), resp. A mechanism of this cleavage of a C=C double bond is discussed. Several substituted enaminonitriles (1e-i) are prepared and the reactivity against aldehydes is studied. Thus, condensation of 3-Amino-2-cyano-crotononitrile (1e) with aldehydes leads to 2-amino-4-phenyl-1,3-butadiene-1,1-dicarbo-nitriles (3). 4-Oxo-2-phenyl-1,2,3,4-tetrahydro-5-pyrimidine-carbonitriles (4) are yielded by the reaction of 3-amino-2-cyano-crotonic-carboxamide (1h) and 3-amino-2-cyano-cinnamamide (1i), resp., with aldehydes. Condensation of 1h and 1i with ethyl ortho-formate leads to 3,4-dihydro-4-oxo-pyrimidine-carbonitriles (6).Keywords
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