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Original Article

ECB. 2014; 3(12): 1026-1030


REACTIONS OF ACENAPHTHENEQUINONE DERIVATIVES WITH SOME AROMATIC AND ALIPHATIC AMINES

Atef M. Amer, Sherif I. Askar, Tarek S. Muhdi.




Abstract

Reaction of acenaphthenequinone and aceanthrenequinone (1a,b) with diaminomaleonitrile at reflux temperature gave acenatho[1,2-
b]pyrazine-8,9-dicarbonitrile and aceanthryleno[1,2-b]pyrazine-10-11-dicarbonitrile (2a,b), respectively. The reaction of 2a,b with
hydrazine hydrate afforded the corresponding cyclic products, 8,11-diaminoacenatho[1,2-b]pyrazino[2,3-d]pyridazine and 10,13-
diaminoaceanthryleno[1,2b]pyrazino[2,3-d]pyridazine (3a,b). The reaction of 1a,b with p-bromoaniline in presence of ZnCl2 afforded
complexes bis(p-bromophenylimino)acenaphthene and -aceanthrene (7a,b). We have also described the synthesis of spiro[2H-aceanthrene2,2'-thiazolidine]-1,4'-dione derivatives (8a,b). Reaction of 1b with 1-amino-3-(N,N-dimethylamino)propane, benzylhydrazine and pbromophenylhydrazine has been investigated for studying the utility of products as pharmacological agents. Chemical and spectroscopic
evidences for the structures of the new compounds are presented.

Key words: Diketones; dinitriles; hydrazones; spiro; thiazolidines






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