SILICA SULFURIC ACID CATALYZED SYNTHESIS OF PYRIMIDINES AND NEW FUSED PYRIMIDO-PURINES via BIGINELLI REACTION
DOI:
https://doi.org/10.15421/jchemtech.v29i4.241661Keywords:
Dihydropyrimidine-2-one, purines, multicomponent reaction, Biginelli reaction, silica sulfuric acid, nucleobasesAbstract
Studies on strategies for the synthesis of pyrimidine derivatives have generated great interest in the chemistry of heterocyclic compounds due to the pharmacological properties of pyrimidines. The most common method for pyrimidine skeleton synthesis is the traditional synthetic approach using the multicomponent Biginelli reaction. A convenient and efficient one-pot three-component synthesis of a new class of pyrimido[1,2-g]purine-7,8-dicarboxylate, pyrimido[2,1-e]purine-8,9-dicarboxylate, and pyrimido[1,6-a]pyrimidine-3,4-dicarboxylate under Biginelli reaction conditions has been described. These compounds were prepared by condensation of sodium diethyl oxalacetate, substituted aromatic aldehyde, and nucleobase (adenine, guanine, or cytosine) using hydrochloric acid, mild heterogeneous solid silica sulfuric acid (SSA), or p-toluenesulfonic acid (TsOH) as a catalyst. The chemical structures of the synthesized compounds were confirmed using infrared spectroscopy (IR), proton (1H) nuclear magnetic resonance (NMR), and mass spectrometric analysis.
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