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http://dx.doi.org/10.5012/jkcs.2009.53.3.308

Pyran and Pyridine as Building Blocks in Heterocyclic Synthesis  

El-Hashash, Maher.A. (Chemistry Department, Faculty of Science, Ain Shams University)
El-Sawy, Abdallah.A. (Chemistry Department, Faculty of Science, Benha University)
Eissa, Abdelmonem.M.F. (Chemistry Department, Faculty of Science, Benha University)
Publication Information
Journal of the Korean Chemical Society / v.53, no.3, 2009 , pp. 308-324 More about this Journal
Abstract
The present work is devoted to study the interaction of $\beta$-aroylacrylic acid derivative (3) with malononitrile in (DMF) in the presence of piperidine and/or ammonium acetate, then using the formed compounds as starting materials for synthesizing fused and isolated heterocyclic systems. It has been established that the $\beta$-aroylacrylic acid (3) reacts with malononitrile in (DMF) in the presence of piperidine as a catalyst with the formation of 4H-pyran derivative (4). By changing the catalyst into ammonium acetate, pyridine derivative (5) has been obtained. Also the N-maleamic acid derivatives (19) and (27) have been synthesized via the interaction of (4) and (5) with maleic anhydride. The purpose of this step is to study the behavior of the formed maleamic acid derivatives – as analogies of $\beta$-aroylacrylic acids – towards different active methylene compounds under Michael addition reaction.
Keywords
$\beta$-Aroylacrylic acid; Michael reaction; 2-aminopyran; 2-aminopyridine; Pyrimidine; Maleamic-acid;
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