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Behaviour of 4-(4-acetoaminophenyl)-4-oxobut- 2-enoic acid towards carbon and nitrogen nucleophiles and use of these products in the synthesis of some interesting heterocycles

M. A. El-Hashasha, S. S .El-Sakkab*, M. H. A. Solimanc, I. I. Abd El-Gwad and M. A. Morsy
 

Abstract

The present work is devoted to study the interaction of -aroylacrylic acid derivative (1) with some containing active methylene compounds under Michael reaction conditions and afforded the Michael adducts (2a-e). When compound 1 was allowed to react with cyclohexanone in the presence of ammonium acetate as catalyst, it afforded hydroquinoline derivative (3). Interaction of the acid 1 with highly and moderately reactive hydrocarbons e.g. p-xylene and acetanilide in the presence of anhydrous aluminum chloride under Friedel-Crafts reaction conditions afforded (4a-b). On the other hand, when the acid 1 was allowed to react with benzyl amine in dry benzene yielded 2-benzylamino- 4-(4-acetaminophenyl)-4-oxobutanoic acid (5). This later compound was used to synthesize some heterocyclic compounds (7-11). Also, aza Michael adduct (6) used as the key starting material for the synthesis of some interesting heterocyclic compounds e.g. pyridazinone, oxazinone and furanone derivatives (13-16).

Key words: -aroylacrylic acid; Michael reaction; Friedel-

Crafts reaction; aza Michael; hydroquinoline.






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