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三羰基炔丙胺的合成及其向2,5-二取代恶唑-4-羧酸酯的转化。

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates.

作者信息

Iwai Kento, Hikasa Akari, Yoshioka Kotaro, Tani Shinki, Umezu Kazuto, Nishiwaki Nagatoshi

机构信息

School of Engineering Science, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan.

出版信息

Beilstein J Org Chem. 2024 Nov 6;20:2827-2833. doi: 10.3762/bjoc.20.238. eCollection 2024.

DOI:10.3762/bjoc.20.238
PMID:39530080
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11552412/
Abstract

The ,-acetal derived from diethyl mesoxalate (DEMO) undergoes elimination of acetic acid upon treatment with a base, leading to the formation of -acylimine in situ. Lithium acetylide readily attacks the imino group to afford ,1,1-tricarbonylated propargylamines. When the resulting propargylamine reacts with butyllithium, ring closure occurs between the ethynyl and carbamoyl groups, yielding 2,5-disubstituted oxazole-4-carboxylates. This cyclization also occurs when the propargylamine is heated with ammonium acetate, resulting in double activation.

摘要

由草酸二乙酯（DEMO）衍生的α-缩醛在用碱处理时会消除乙酸，从而原位形成α-酰亚胺。乙炔锂很容易进攻亚氨基，得到α,1,1-三羰基化炔丙胺。当生成的炔丙胺与丁基锂反应时，乙炔基和氨基甲酰基之间会发生环化反应，生成2,5-二取代的恶唑-4-羧酸盐。当炔丙胺与乙酸铵一起加热时也会发生这种环化反应，从而实现双重活化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/a589d92b4f53/Beilstein_J_Org_Chem-20-2827-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/30d9159cd770/Beilstein_J_Org_Chem-20-2827-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/b26cb94bee5f/Beilstein_J_Org_Chem-20-2827-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/d2798d89ef05/Beilstein_J_Org_Chem-20-2827-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/a589d92b4f53/Beilstein_J_Org_Chem-20-2827-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/30d9159cd770/Beilstein_J_Org_Chem-20-2827-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/b26cb94bee5f/Beilstein_J_Org_Chem-20-2827-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/d2798d89ef05/Beilstein_J_Org_Chem-20-2827-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f841/11552412/a589d92b4f53/Beilstein_J_Org_Chem-20-2827-g005.jpg

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3
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ChemistryOpen. 2023 Apr;12(4):e202200223. doi: 10.1002/open.202200223. Epub 2023 Jan 31.
4
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