1,3-偶极环加成反应腈亚胺与二氧化碳：通往 1,3,4-恶二唑-2(3H)-酮。
1,3-Dipolar Cycloaddition of Nitrile Imine with Carbon Dioxide: Access to 1,3,4-Oxadiazole-2(3H)-ones.
机构信息
State Key Laboratory of Fine Chemicals, Dalian University of Technology , Dalian, 116024, P. R. China.
出版信息
J Org Chem. 2017 Jul 21;82(14):7637-7642. doi: 10.1021/acs.joc.7b00963. Epub 2017 Jul 5.
Efficient synthesis of 1,3,4-oxadiazole-2(3H)-one was achieved by CsF/18-crown-6 mediated 1,3-dipolar cycloaddition of nitrile imine and 2.0 MPa of CO. CsF/18-crown-6 played a key role in enhancing the reactivity of CO as a 1,3-dipolarophile. The practical utility of this transition-metal-free approach to 1,3,4-oxadiazole-2(3H)-one is highlighted by the convenient synthesis of a commercial herbicide Oxadiazon and a MAO B inhibitor.
通过 CsF/18-冠-6 介导的腈亚胺与 2.0 MPa 的 CO 的 1,3-偶极环加成反应，高效合成了 1,3,4-噁二唑-2(3H)-酮。CsF/18-冠-6 在增强 CO 作为 1,3-偶极体的反应性方面发挥了关键作用。这种无过渡金属方法合成 1,3,4-噁二唑-2(3H)-酮的实际应用，通过方便地合成商业除草剂恶唑酮和 MAO B 抑制剂得到了突出体现。
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