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2,4-噻唑烷二酮的合成方法、路线与机理研究进展

Progress in the Synthesis Methods, Routes, and Mechanisms of 2,4-Thiazolidinedione

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【作者】 王培张天行竺宁

【Author】 Wang Pei;Zhang Tianxing;Zhu Ning;College of Chemical Engineering, Inner Mongolia University of Technology;Key Laboratory of College of Carbon Dioxide Resource Utilization;Inner Mongolia Autonomous Region CO2 Capture and Resource Engineering Technology Research Center;

【通讯作者】 张天行;竺宁;

【机构】 内蒙古工业大学化工学院,二氧化碳资源化利用自治区高等学校重点实验室,内蒙古自治区CO2捕集与资源化工程技术研究中心

【摘要】 2,4-噻唑烷二酮是一种重要的医药中间体,已经被广泛应用于抗高血糖、抗癌、抗菌、抗病毒等方面,具有广阔的市场前景。首先,通过逆合成法对2,4-噻唑烷二酮五元环的构建方式进行系统分析,按照硫源的引入方式将合成方案分为硫脲法、硫氰酸盐法、羰基硫法和罗丹宁法四类,并对2,4-噻唑烷二酮合成过程中的取代、环化、水解反应机制进行探讨。其次,探究了不同合成方法的反应机理,阐明不同反应原料的反应速率、原子经济性,并针对各自的优缺点进行了评价。最后,根据逆合成分析结果提出两种潜在的合成策略,为开发绿色高效、环境友好、适合工业化生产的2,4-噻唑烷二酮及其类似结构药物的合成方法提供理论基础和研究思路。

【Abstract】 2,4-Thiazolidinedione is a crucial pharmaceutical intermediate, which has found extensive applications in diverse fields like antihyperglycemia, anticancer, antibacterial, antiviral, etc., offering vast market prospects. Firstly, this review presented a systematical analysis of the construction methods of the five-membered ring of 2,4-thiazolidinedione via retrosynthetic analysis. Based on the introduction of sulfur sources, the synthesis schemes were categorized into four classes: thiourea method, thiocyanate method, carbonyl sulfur method, and rhodanine method. And the substitution, cyclization, and hydrolysis reaction mechanisms in the synthesis process of 2,4-thiazolidinedione were discussed. Then, the reaction mechanisms of different synthesis methods were explored, and the reaction rate and atomic economy of different reaction raw materials were clarified. Their respective advantages and disadvantages were evaluated, and two potential synthesis strategies were proposed. Finally, this review provided a theoretical basis and research ideas for the development of green, efficient, environmentally friendly, and suitable synthesis methods for 2,4-thiazolidinedione and its similar structural drugs in industrial production.

【基金】 内蒙古科技计划项目(2021GG0335);内蒙古自然科学基金项目(2021ZD02,2022LHQN2003);内蒙古自治区高等学校CO2资源化利用创新团队项目(NMGIRT2212);自治区直属高校基本科研业务费项目(JY20220106);内蒙古工业大学科学研究项目(ZZ202109)资助
  • 【分类号】TQ463
  • 【下载频次】95
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