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通过炔丙基/烯丙基异构化由()-2-烯-4-炔-1-醇制备4-亚丙基恶唑啉

Preparation of 4-Allenyloxazolines from ()-2-En-4-yn-1-ol via Propargyl/Allenyl Isomerization.

作者信息

Hung Shi-Heng, Wang Yu-Min, Liu Yi-Hung, Liu Shiuh-Tzung

机构信息

Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.

出版信息

J Org Chem. 2024 Sep 6;89(17):12762-12768. doi: 10.1021/acs.joc.4c01152. Epub 2024 Aug 23.

DOI:10.1021/acs.joc.4c01152
PMID:39177357
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11382262/
Abstract

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

摘要

描述了一种通过2-烯-4-炔-1-醇与三氯乙腈在DBU存在下反应制备4-烯丙基恶唑啉的新方法。反应通过2-烯-4-炔-1-醇中OH官能团对CClCN的亲核进攻，随后进行环化、炔丙基/丙二烯异构化和质子化。在本研究中，注意到炔丙基/丙二烯异构化对取代基敏感。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/3eeaac5116b7/jo4c01152_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/e21aefb35a49/jo4c01152_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/e90532e2b4f8/jo4c01152_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/7dc3a3d99687/jo4c01152_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/3eeaac5116b7/jo4c01152_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/e21aefb35a49/jo4c01152_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/e90532e2b4f8/jo4c01152_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/7dc3a3d99687/jo4c01152_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a77e/11382262/3eeaac5116b7/jo4c01152_0004.jpg

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本文引用的文献

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