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

Abstract

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).