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Utility of 4-(4-acetoaminophenyl)-4-oxobut-2-enoic acid to Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis

M. A. El-Hashasha, M. H. A. Solimanb, I. I. Abd El-Gwadc, S. S. El-Sakkac* and M. A. Morsy
 

Abstract

 

The present work is devoted to study the interaction of -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. It has been established that the -aroylacrylic acid (1) react with malononitrile in (DMF) in the presence of piperidine as catalyst with formation of 4H-pyran derivative (2). By changing the catalyst into ammonium acetate, pyridine derivative (3) has been obtained. When compound (2) was allowed to react with triethylorthoformate afforded ethoxymethyleneamino- 4H-pyran (4). Compound (4) was used as key 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 as analogies of -aroylacrylic towards different active methylene compounds under Michael addition reaction (10-14); (16-18).         

Keywords: -aroylacrylic acid, Michael addition, 2-aminopyran,

2-aminopyridine, pyrimidine and maleamic acid






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