REACTIONS OF ARYLIDENETETRALONES WITH DERIVATES OF CYANOACETIC ACID - HETEROCYCLES BY MICHAEL REACTIONS IV

Some reactions of 2-arylidene-tetralones 1 with cyanoacetamide and alkyl cyanoacetates under basic conditions are described. From 1 and cyanoacetamide the benzo[h]quinoline-2-ones 3 are formed by cyclization with the carboxamide group, the intermediate addition product 2 is not isolable. The addition products 5 from 1 and cyanoacetates however are crystalline compounds, which are converted by cyclization via the ester group to lactones 6, and then oxidized to 7. The expected products from a cyclization with the cyanide group are not found. The possibility of this cyclization path is shown by reaction of 5 to the tetracyclus 10 whose structure is found to be analogue to that of the reaction product from 11-obtained by reaction from 1 and malononitrile-to 12. © 1979 Springer-Verlag.