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<p>This research introduces a groundbreaking bifunctional ionic catalyst, L-proline taurinate, synthesized in water using biodegradable materials, aligning with green chemistry principles. The structure of the synthesized catalyst was characterized using FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and HRMS. The ionic nature of the catalyst was validated through density functional theory analysis. The catalyst demonstrated exceptional efficiency in the green synthesis of 2-amino-3-cyano-4<i>H</i>-pyrans and pyran-annulated heterocyclic scaffolds. A total of 23 compounds were synthesized in less than 10&#xa0;min with excellent yields (86–98%), through the Knoevenagel-Michael-cyclization coupling reaction of aldehydes, 1,3-diketones, and malononitrile. The substrate versatility was demonstrated with substituted aromatic and heterocyclic aldehydes, along with 1,3-dicarbonyl compounds like dimedone, 1,3-cyclohexanedione, and 4-hydroxy-2<i>H</i>-chromen-2-one, as well as barbituric acid, 2-thiobarbituric acid, and 3-methyl-1-phenyl-2-pyrazoline-5-one. This robust protocol boasts features such as one-pot, single-step, three-component operations, easy catalyst separation and recycling potential, broad applicability to various substrates, and suitability for gram-scale production. This innovative approach represents a major stride in sustainable catalytic technology and green chemical procedures, paving the way for future advancements in eco-friendly synthesis techniques.</p> Graphical Abstract <p></p>

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Synthesis and Application of L-Proline Taurinate as a Novel Bifunctional Ionic Catalyst for the Highly Efficient Synthesis of 2-Amino-3-Cyano-4H-Pyrans and Pyran-Annulated Heterocycles

  • 期刊论文

  • 发表日期：

    2025年1月2日

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  • Sunita Teli,
  • Shivani Soni,
  • Pankaj Teli,
  • Mehul Darji,
  • Anu Manhas,
  • Shikha Agarwal

摘要

This research introduces a groundbreaking bifunctional ionic catalyst, L-proline taurinate, synthesized in water using biodegradable materials, aligning with green chemistry principles. The structure of the synthesized catalyst was characterized using FT-IR, 1H NMR, 13C NMR, and HRMS. The ionic nature of the catalyst was validated through density functional theory analysis. The catalyst demonstrated exceptional efficiency in the green synthesis of 2-amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds. A total of 23 compounds were synthesized in less than 10 min with excellent yields (86–98%), through the Knoevenagel-Michael-cyclization coupling reaction of aldehydes, 1,3-diketones, and malononitrile. The substrate versatility was demonstrated with substituted aromatic and heterocyclic aldehydes, along with 1,3-dicarbonyl compounds like dimedone, 1,3-cyclohexanedione, and 4-hydroxy-2H-chromen-2-one, as well as barbituric acid, 2-thiobarbituric acid, and 3-methyl-1-phenyl-2-pyrazoline-5-one. This robust protocol boasts features such as one-pot, single-step, three-component operations, easy catalyst separation and recycling potential, broad applicability to various substrates, and suitability for gram-scale production. This innovative approach represents a major stride in sustainable catalytic technology and green chemical procedures, paving the way for future advancements in eco-friendly synthesis techniques.

Graphical Abstract