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

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 aluminumchloride 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 asthe key starting material for the synthesis of some interesting heterocyclic compounds e.g. pyridazinone, oxazinoneand furanone derivatives (13-16)

Utility of 4-(4-acetoaminophenyl)-4-oxo-but-2-enoic acid to prepare Pyranand Pyridine derivatives as building blocks in Heterocyclic Synthesis

The present work is devoted to study the interaction of β -aroylacrylic acid derivative (1) with malononitrile in the presence of piperidine and/or ammonium acetate, then using the formed compounds as a starting material for synthesizing fused and isolated heterocyclic system. Ithas been established that the β-aroylacrylic acid (1) reactwith malononitrile in (DMF) in the presence of piperidineas catalyst with formation of 4H-pyran derivative (2). Bychanging the catalyst into ammonium acetate, pyridine derivative (3) has been obtained. When compound (2) wasallowed to react with triethylorthoformate afforded ethoxymethyleneamino-4H-pyran (4). Compound (4) was used askey starting material for synthesizing some interesting annulated and heterocyclic systems (5-8). Also, the maleamic acid derivatives (9) and (15) have been synthesized via the interaction of (2) and (3) with maleic anhydride to study the behavior of the formed maleamic acid derivatives asanalogies of β-aroylacrylic towards different active methylene compounds under Michael addition reaction (10-14); (16-18)