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Preparation of 4-Allenyloxazolines from (Z)-2-En-4-yn-1-ol via Propargyl/Allenyl Isomerization
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-08-23 , DOI: 10.1021/acs.joc.4c01152
Shi-Heng Hung, Yu-Min Wang, Yi-Hung Liu, Shiuh-Tzung Liu

A novel method for the preparation of 4-allenyl-oxazolines 2 is described via the reaction of 2-en-4-yn-1-ols 1 with trichloroacetonitrile in the presence of DBU. Reaction proceeds through the nucleophilic attack of OH functionality in 1 to CCl3CN followed by cyclization, propargyl/allene isomerization, and protonation. In this investigation, it is noticed that propargyl/allene isomerization is sensitive to the substituents.

中文翻译:


(Z)-2-En-4-yn-1-ol 通过炔丙基/丙二烯基异构化制备 4-联烯基恶唑啉



描述了一种通过 2-en-4-yn-1-ols 1与三氯乙腈在 DBU 存在下反应制备 4-烯基-恶唑啉2的新方法。反应通过1中的 OH 官能团的亲核攻击生成 CCl 3 CN,然后进行环化、炔丙基/丙二烯异构化和质子化。在这项研究中,注意到炔丙基/丙二烯异构化对取代基敏感。
更新日期:2024-08-23
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