Scholarlink

<p>This study presents a novel approach for synthesizing various regio-selective 3,5-disubstituted isoxazoles using inexpensive CuI catalysis. Moderate to good yields of the target compounds were achieved through this method. Based on the experimental results and literature insights, a plausible mechanism involving two consecutive Cu-catalytic cycles, Sonogashira coupling, and intramolecular cyclization was proposed. Notably, opposite regio-selectivity was observed between products obtained from uncatalyzed and CuI-catalyzed reactions. The outcomes of this CuI-catalyzed one-pot protocol represent an improvement over previous methods, offering a promising avenue for diverse isoxazole derivative synthesis. The proposed process involves homogeneous CuI-promoted one-pot three-component regio-selective synthesis of 3,5-disubstituted isoxazoles, with key <i>in situ</i> α,β-unsaturated ynone intermediates crucial for subsequent reactions. This approach streamlines synthesis, allowing simultaneous assembly of multiple chemical components in a single reaction vessel, while minimizing the need for complex steps and costly reagents. Overall, this strategy holds promise for rapid and economical production of diverse 3,5-disubstituted isoxazoles, with potential applications in medicinal chemistry and materials science.</p> Graphical abstract <p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

One-pot regio-selective synthesis of 3,5-disubstituted isoxazoles via CuI catalyzed consecutive acyl Sonogashira coupling and intramolecular cyclization

  • 期刊论文

  • 发表日期：

    2025年9月20日

查看全文
  • Siva Kumar Rapeti,
  • Rapeti Thrinadh Kumar,
  • Makam Parameshwar,
  • B B V Sailaja,
  • Jayaprakash Kanijam Raghupathi,
  • Naresh Kumar Katari

摘要

This study presents a novel approach for synthesizing various regio-selective 3,5-disubstituted isoxazoles using inexpensive CuI catalysis. Moderate to good yields of the target compounds were achieved through this method. Based on the experimental results and literature insights, a plausible mechanism involving two consecutive Cu-catalytic cycles, Sonogashira coupling, and intramolecular cyclization was proposed. Notably, opposite regio-selectivity was observed between products obtained from uncatalyzed and CuI-catalyzed reactions. The outcomes of this CuI-catalyzed one-pot protocol represent an improvement over previous methods, offering a promising avenue for diverse isoxazole derivative synthesis. The proposed process involves homogeneous CuI-promoted one-pot three-component regio-selective synthesis of 3,5-disubstituted isoxazoles, with key in situ α,β-unsaturated ynone intermediates crucial for subsequent reactions. This approach streamlines synthesis, allowing simultaneous assembly of multiple chemical components in a single reaction vessel, while minimizing the need for complex steps and costly reagents. Overall, this strategy holds promise for rapid and economical production of diverse 3,5-disubstituted isoxazoles, with potential applications in medicinal chemistry and materials science.

Graphical abstract