硬币金属催化的未充分探索的β-炔丙基酰肼的发散性杂环化反应
Coinage Metal-Catalyzed Divergent Heterocyclizations of Underexplored -Propargyl Hydrazides.
作者信息
Diez-Iriepa Daniel, Toledano-Pinedo Mireia, Herrera-Hernández Lorena, Samadi Abdelouahid, Raouf Yasir S, Rodríguez-Fernández M Mercedes, Flores-Galán Paula, Yanai Hikaru, Alonso José M, Marco-Contelles José, Almendros Pedro
机构信息
Department of Chemistry, College of Science, United Arab Emirates University, Al Ain 15551, United Arab Emirates.
Instituto de Química Orgánica General (IQOG), Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
出版信息
Org Lett. 2025 Sep 5;27(35):9753-9758. doi: 10.1021/acs.orglett.5c03069. Epub 2025 Aug 27.
Herein, we disclose metal-catalyzed tunable annulations of uncharted alkyne-tethered hydrazides for the divergent preparation of diazacyclic frameworks. Cationic gold facilitates the O-cyclization, providing valuable [1,3,4]oxadiazine scaffolds with total selectivity, whereas silver catalysis promotes controlled N-cyclization to access -acyl pyrazoles. Furthermore, density-functional-theory-based theoretical investigations support two different pathways (ionic versus radical) operating in the catalytic heterocyclization reaction of the same -propargyl hydrazide substrate.
在此，我们披露了金属催化的未知炔基连接酰肼的可调环化反应，用于发散性制备二氮杂环骨架。阳离子金促进O-环化反应，以完全选择性提供有价值的[1,3,4]恶二嗪支架，而银催化促进可控的N-环化反应以获得β-酰基吡唑。此外，基于密度泛函理论的理论研究支持在相同的β-炔丙基酰肼底物的催化杂环化反应中存在两种不同的途径（离子型与自由基型）。
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