Abstract
Some reactions of 2-arylidene-tetralones1 with cyanoacetamide and alkyl cyanoacetates under basic conditions are described. From1 and cyanoacetamide the benzo[h]quinoline-2-ones3 are formed by cyclization with the carboxamide group, the intermediate addition product2 is not isolable. The addition products5 from1 and cyanoacetates however are crystalline compounds, which are converted by cyclization via the ester group to lactones6, and then oxidized to7. The expected products from a cyclization with the cyanide group are not found. The possibility of this cyclization path is shown by reaction of5 to the tetracyclus10 whose structure is found to be analogue to that of the reaction product from11-obtained by reaction from1 and malononitrile-to12.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literatur
H.-H. Otto, O. Rinus undH. Schmelz, Mh. Chem.110, 115 (1979).
H.-H. Otto, Mh. Chem.109, 681 (1978).
E. P. Kohler undB. L. Souther, J. Amer. Chem. Soc.44, 2903 (1922).
A. Sammour, A. Rouf, M. Elkasaby undM. Hassan, J. Prakt. Chem.315, 1175 (1973).
Author information
Authors and Affiliations
Additional information
3. Mitt.:H.-H. Otto, O. Rinus undH. Schmelz, Synthesis1978, 681.
Rights and permissions
About this article
Cite this article
Otto, HH., Schmelz, H. Reaktionen von Arylidentetralonen mit Cyanessigsäurederivaten. Monatshefte für Chemie 110, 249–256 (1979). https://doi.org/10.1007/BF00911912
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00911912