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.

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.