Synthesis of [6,5,5]Ring-Fused Tricyclic Triazoles by Copper-Promoted Double Cyclization

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-25 DOI:10.1002/ejoc.202400736

Martin Pošta, Margarita Dmitrieva, Chiara Volpe, Václav Matoušek, Blanka Klepetářová, Petr Beier

引用次数: 0

Abstract

Copper(I)-mediated azide-alkyne cycloaddition was coupled with cross-coupling for the synthesis of [6,5,5] ring-fused tricyclic triazoles. Copper(I)-mediated azide-alkyne cycloaddition was investigated on 2-iodoaryl propynes or propynones. With catalytic amount of Cu(I) salts or with N-donor ligands on copper only the products of azide-alkyne cycloadditions were formed. However, with an equimolar amount of copper(I) iodide and triethylamine new [6,5,5] ring-fused tricyclic triazoles were formed by azide-alkyne cycloadditon coupled to a cross-coupling reaction.

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通过铜促进的双环化合成[6,5,5]环融三环三唑

将铜(I)介导的叠氮-炔环化反应与交叉耦合结合起来，合成了[6,5,5] 环融合的三环三唑。研究了铜(I)介导的叠氮-炔环化反应在 2-碘芳基丙炔或丙炔酮上的应用。在催化 Cu(I) 盐或铜上的 N-供体配体的情况下，只能形成叠氮-炔环化产物。然而，在等摩尔量的碘化铜（I）和三乙胺的作用下，叠氮-炔环加成反应与交叉耦合反应生成了新的[6,5,5] 环融合三环三唑。

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.