O. Tsuge, A. Torii
1973
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
In the presence of aqueous sodium hydroxide, 9-ethynylacridine (I) reacts with malononitrile and with ethyl cyanoacetate to yield the corresponding 1,1-disubstituted 3-(9-acridanylidene)propenes III. A similar reaction of I with diethyl malonate affords a 2:1 adduct VI and a 1:2 adduct VII. On the other hand, I reacts with acetylacetone to give 3-acetyl-5-(9-acridanylidene)-1-(9-acridinyl)pent-1,3-diene (IX). In this context, the reaction of 9-chloroacridine (XI) with active methylene compounds has been reinvestigated; XI reacts with malononitrile and with ethyl cyanoacetate to afford products XII with an acridane structure, while with diethyl malonate XI gives 9-di(ethoxycarbonyl)methylacridine (XIII), as has been reported previously.