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<p>We present the synthesis of a novel series of tri-substituted methane (TRSM) derivatives via an efficient one-pot, three-component reaction. This reaction combines 4-hydroxybenzo[h]quinolin-2(1<i>H</i>)-one, aromatic aldehydes, and 1,3-dimethyl-6-aminouracil, catalyzed by L-proline in ethanol. Our primary aim is to create a new TRSM scaffold by incorporating diverse pharmacophore moieties into a unified structure, providing a foundation for future drug discovery and medicinal chemistry studies. Key advantages of this approach include the use of an organocatalyst, a streamlined experimental process, and the absence of toxic byproducts. Notably, the methodology eliminates the need for time-consuming column chromatography, offering a cleaner, more efficient synthesis. The chemical structures of the products were confirmed through IR, NMR, mass spectrometry, and elemental analysis, validating the successful formation of the desired derivatives.</p>

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Diversity-oriented synthesis of novel benzo[h]quinoline and pyrimidine-tethered tri-substituted methane using L-proline as an effective bio-organo-catalyst

  • 期刊论文

  • 发表日期：

    2025年7月18日

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  • Sajedeh Alizadeh,
  • Abbas Ali Esmaeili

摘要

We present the synthesis of a novel series of tri-substituted methane (TRSM) derivatives via an efficient one-pot, three-component reaction. This reaction combines 4-hydroxybenzo[h]quinolin-2(1H)-one, aromatic aldehydes, and 1,3-dimethyl-6-aminouracil, catalyzed by L-proline in ethanol. Our primary aim is to create a new TRSM scaffold by incorporating diverse pharmacophore moieties into a unified structure, providing a foundation for future drug discovery and medicinal chemistry studies. Key advantages of this approach include the use of an organocatalyst, a streamlined experimental process, and the absence of toxic byproducts. Notably, the methodology eliminates the need for time-consuming column chromatography, offering a cleaner, more efficient synthesis. The chemical structures of the products were confirmed through IR, NMR, mass spectrometry, and elemental analysis, validating the successful formation of the desired derivatives.