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Abstract <p>We report the synthesis of pyrimidine-type products based on the three-component reaction between 3-nitrobenzaldehyde, ammonium acetate, and a variety of 1,3-dicarbonyl compounds in isopropanol at room temperature. This methodology is a modification of the well-documented Hantzsch synthesis, yet deviates from the generally expected dihydropyridine products, due to the change in stoichiometry. The resulting tetrahydropyrimidine products were obtained in moderate to high yields (65–83%) and characterized by multiple methods, such as <sup>1</sup>H, <sup>13</sup>C, DEPT-<sup>13</sup>C-NMR, and HR-MS. From this preliminary investigation, we seek to confirm the mechanism of this reaction as an unusual route of the famous Hantzsch dihydropyridine synthesis.</p>

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Synthesis and Cyclization Mechanism of Pyrimidine-type Heterocycles Based on the Modified Hantzsch Reaction

  • 期刊论文

  • 发表日期：

    2026年2月1日

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  • Tri T. T. Phan,
  • Tung H. To

摘要

Abstract

We report the synthesis of pyrimidine-type products based on the three-component reaction between 3-nitrobenzaldehyde, ammonium acetate, and a variety of 1,3-dicarbonyl compounds in isopropanol at room temperature. This methodology is a modification of the well-documented Hantzsch synthesis, yet deviates from the generally expected dihydropyridine products, due to the change in stoichiometry. The resulting tetrahydropyrimidine products were obtained in moderate to high yields (65–83%) and characterized by multiple methods, such as 1H, 13C, DEPT-13C-NMR, and HR-MS. From this preliminary investigation, we seek to confirm the mechanism of this reaction as an unusual route of the famous Hantzsch dihydropyridine synthesis.