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2-氮杂环丙烯在铜催化的叠氮化物-炔烃环加成反应中的反应活性

Reactivity of 2-Azirines in Copper-Catalyzed Azide-Alkyne Cycloaddition Reactions.

作者信息

Janecký Lukáš, Madabeni Andrea, Jelínková Eliška, Klepetářová Blanka, Rulíšek Lubomír, Beier Petr

机构信息

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic.

Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, CZ-128 43 Prague 2, Czech Republic.

出版信息

Org Lett. 2025 Sep 12;27(36):10077-10081. doi: 10.1021/acs.orglett.5c03150. Epub 2025 Sep 1.

DOI:10.1021/acs.orglett.5c03150
PMID:40889290
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12442078/
Abstract

A reaction between azide, alkyne and 2-azirine resulted in C-C bond formation at position five of 1,2,3-triazole, instead of previously misidentified C-N bond connectivity. The reaction mechanism of this C-C bond formation on the triazole ring was fully explained by employing calibrated QM(DFT-D3) calculations. Functionalization of primary products provided substituted pyrimidine, furan or 1,3-oxazepine.

摘要

叠氮化物、炔烃和2-氮杂环丙烷之间的反应在1,2,3-三唑的5位形成了C-C键，而非之前错误认定的C-N键连接方式。通过采用校准的量子力学（密度泛函理论-D3）计算，充分解释了三唑环上这种C-C键形成的反应机理。初级产物的官能团化提供了取代嘧啶、呋喃或1,3-氧氮杂环庚烷。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/b3058cbe8b0b/ol5c03150_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/50457d2d94f3/ol5c03150_0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/63ad26394d92/ol5c03150_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/14f7383b5f2d/ol5c03150_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/21203a2ed3ca/ol5c03150_0006.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/dc427488b0d4/ol5c03150_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/29fda378c963/ol5c03150_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/b3058cbe8b0b/ol5c03150_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/50457d2d94f3/ol5c03150_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/b65928915446/ol5c03150_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/63ad26394d92/ol5c03150_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/14f7383b5f2d/ol5c03150_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/21203a2ed3ca/ol5c03150_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/ea392cdb13a9/ol5c03150_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/dc427488b0d4/ol5c03150_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/29fda378c963/ol5c03150_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae19/12442078/b3058cbe8b0b/ol5c03150_0001.jpg

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本文引用的文献

1
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RSC Adv. 2024 Aug 27;14(37):26938-26942. doi: 10.1039/d4ra04794j. eCollection 2024 Aug 22.
2
Lewis acid-mediated transformations of 5-acyl--fluoroalkyl-1,2,3-triazoles to cyclopentenones, indenones, or oxazoles.路易斯酸介导的5-酰基-氟烷基-1,2,3-三唑向环戊烯酮、茚酮或恶唑的转化反应
RSC Adv. 2024 Apr 25;14(19):13640-13645. doi: 10.1039/d4ra01707b. eCollection 2024 Apr 22.
3
Synthesis and Cycloaddition Reactions of 1-Azido-1,1,2,2-tetrafluoroethane.
1-叠氮基-1,1,2,2-四氟乙烷的合成与环加成反应
J Org Chem. 2023 Nov 3;88(21):14969-14977. doi: 10.1021/acs.joc.3c01346. Epub 2023 Oct 20.
4
Interrupted Click Reaction with CuCFCF Reagent: Synthesis of 5-Pentafluoroethyl 1,2,3-Triazoles.CuCFCF 试剂中断点击反应：5-全氟乙基 1,2,3-三唑的合成。
Org Lett. 2023 Jul 7;25(26):4945-4949. doi: 10.1021/acs.orglett.3c01855. Epub 2023 Jun 23.
5
Synthesis of Azidodifluoromethyl Phenyl Sulfone and Its Use as a Synthetic Equivalent of the Azidodifluoromethyl Anion.叠氮二氟甲基苯砜的合成及其作为叠氮二氟甲基阴离子的合成等价物的用途。
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Chemistry. 2020 Jan 16;26(4):773-782. doi: 10.1002/chem.201903627. Epub 2019 Nov 6.