通过腈亚胺与有机氰酰胺的选择性逐步环加成合成 1,2,4-三唑-3-亚胺。
Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides.
机构信息
La Trobe Institute for Molecular Science , La Trobe University , Bundoora , VIC 3086 , Australia.
School of Chemistry, Joseph Banks Laboratory , University of Lincoln , Lincoln , LN6 7DL , U.K.
出版信息
Org Lett. 2018 Jul 20;20(14):4263-4266. doi: 10.1021/acs.orglett.8b01673. Epub 2018 Jun 28.
A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.
报道了一种通过有机氰酰胺离子与腈亚胺双自由基的选择性、形式上的 1,3-偶极环加成反应合成 1,2,4-三唑-3-亚胺的简便方法。1,2,4-三唑-3-亚胺的水解生成相应的 1,2,4-三唑-5-酮。通过 DFT 计算支持的逐步反应机理来解释反应的选择性。
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