Divergent Synthesis of 4‐Aminotriazoles Through Click Cycloaddition and Generation of Iodonium(III) Triazoles

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-12-17 DOI:10.1002/ejoc.202401273
Takumi Hayashi, Elghareeb E. Elboray, Hina Sudo, Naoko Takenaga, Hiroyuki Satake, Toshifumi Dohi
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Abstract

The divergent synthesis of 4‐amino‐1,2,3‐triazoles was accomplished through the Cu‐catalyzed cycloaddition of organic azides with alkynyliodonium(III) salts, followed by Cu‐catalyzed triazole‐amine coupling involving treatment with amines and amides. The in situ formation of 1,2,3‐triazole iodonium salts is crucial to this approach, and the utilization of a Cu‐catalyst facilitates cycloaddition and C‐N bond formation. The synthesis of 1,2,3‐triazolyliodonium(III) salts proposed in this study offers advantages, including mild reaction conditions, a broad substrate scope, and operational simplicity, while also providing efficient access to a complex and diverse range of 4‐amino‐1,2,3‐triazole derivatives.
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通过铜催化有机叠氮化物与炔基碘鎓(III)盐的环化反应,然后在铜催化下用胺和酰胺处理三唑-胺偶联,完成了 4-氨基-1,2,3-三唑的发散合成。原位形成 1,2,3-三唑碘鎓盐对这种方法至关重要,而使用铜催化剂则有利于环化和 C-N 键的形成。本研究提出的 1,2,3-三氮唑碘鎓(III)盐的合成方法具有反应条件温和、底物范围广、操作简单等优点,同时还能有效地获得复杂多样的 4-氨基-1,2,3-三氮唑衍生物。
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来源期刊
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.
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