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<p>A simple and efficient method has been established for synthesizing N-(2-fluoro-4-nitrophenyl)pyridin-2-amine and N-(2-fluoro-4-nitrophenyl)-5-phenyl-1,3-thiazol-2-amine via a nucleophilic aromatic substitution (SNAr) pathway. In this protocol, heteroaryl amines are first deprotonated using sodium hydride (NaH) in dimethylformamide (DMF), generating the corresponding nucleophilic species. These intermediates subsequently react with 2-fluoro-4-nitrobenzene, where the strongly electron-withdrawing nitro substituent activates the aromatic ring, allowing smooth displacement of the fluorine atom. The reaction proceeds under mild, metal-free conditions and consistently provides high yields, making it both cost-effective and operationally convenient. The resulting N-(fluoro-nitrophenyl) heterocyclic amines represent valuable building blocks for the development of biologically active compounds and functional organic materials. Preliminary biological screening of the synthesized molecules further indicates promising activity, underscoring their potential relevance in future medicinal and pharmaceutical research.</p>

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Efficient synthesis of novel N-(2-fluoro-4-nitrophenyl) heteroaryl amines via NaH/DMF-promoted nucleophilic aromatic substitution and assessment of their biological activities

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月28日

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  • Nayan Adsul,
  • Surekha N. Jadhav,
  • Rahul M. Mane,
  • Kishor V. Gaikwad

摘要

A simple and efficient method has been established for synthesizing N-(2-fluoro-4-nitrophenyl)pyridin-2-amine and N-(2-fluoro-4-nitrophenyl)-5-phenyl-1,3-thiazol-2-amine via a nucleophilic aromatic substitution (SNAr) pathway. In this protocol, heteroaryl amines are first deprotonated using sodium hydride (NaH) in dimethylformamide (DMF), generating the corresponding nucleophilic species. These intermediates subsequently react with 2-fluoro-4-nitrobenzene, where the strongly electron-withdrawing nitro substituent activates the aromatic ring, allowing smooth displacement of the fluorine atom. The reaction proceeds under mild, metal-free conditions and consistently provides high yields, making it both cost-effective and operationally convenient. The resulting N-(fluoro-nitrophenyl) heterocyclic amines represent valuable building blocks for the development of biologically active compounds and functional organic materials. Preliminary biological screening of the synthesized molecules further indicates promising activity, underscoring their potential relevance in future medicinal and pharmaceutical research.