通过4--1,2,4-triazoline-3,5-dione和alkynes之间的正式 [3+2] 循环添加,合成中性 triazolones
Yusuke Kuroda1,2, Maya Krell1,3, Kazuma Kurokawa1
1Graduate School of Pharmaceutical Sciences, Kyoto University Yoshida, Kyoto 606-8501, Japan. kuroday@pharm.kyoto-u.ac.jp.
这项研究探讨了1,2,4-triazoline-3,5-diones (TADs) 和之间的反应. 我们发现1,1,1,3,3,3-hexafluoro-2-propanol能够进行一种新的 [3+2] 循环添加,形成独特的介质三醇.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
背景情况:
- 1,2,4-Triazoline-3,5-diones (TADs) 是化学科学中广泛使用的高度反应的试剂.
- TADs与不和碳化合物的反应性已得到充分证实,但它们与基因的反应仍未得到充分研究.
研究的目的:
- 为了研究TADs和基之间的反应.
- 探索使用1,1,1,3,3,3-hexafluoro-2-propanol作为这种反应的促进剂.
- 为了合成和描述新型中介离子三醇.
主要方法:
- [3+2]4--1,2,4-三-3,5-和各种基之间的循环添加反应.
- 使用1,1,1,3,3,3-六二醇作为反应介质.
- 使用X射线衍射分析进行结构性表征.
- 使用密度函数理论 (DFT) 计算的计算分析.
主要成果:
- 这种反应成功地产生了前所未有的中介离子三醇.
- 发现1,1,1,3,3,3-hexafluoro-2-propanol可以促进 [3+2] 循环添加.
- 合成的三类的结构通过X射线衍射和DFT证实了.
结论:
- 开发了一种新且高效的 [3+2] 循环添加反应,用于TAD和基.
- 这种方法使得人们可以接触到一类新的中介离子三醇.
- 这项研究扩大了TADs已知的反应性,并提供了对它们与基因的反应机制的见解.
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相关概念视频
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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