期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 6, 页码 4058-4066出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03070
关键词
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资金
- National Natural Science Foundation of China [21502042]
- Scientific Research Key Project Fund of Henan Provincial Education Department [20A150002]
- Postdoctoral Science Foundation of Henan University [232939]
A direct strategy for the selective synthesis of 3-acyl-1,2,4-oxadiazoles from alkynes and nitriles has been developed under iron(III) nitrate-mediated conditions. The mechanism includes three sequential procedures: iron(III) nitrate-mediated nitration of alkynes leads to alpha-nitroketones, dehydration of anitroketones provides the nitrile oxides, and 1,3-dipolar cycloaddition of nitrile oxides with nitriles produces 3-acyl-1,2,4-oxadiazoles under iron-mediated conditions. Iron(III) nitrate plays dual roles in the nitration of alkynes and the activation of nitriles, while the formation of pyrimidine/isoxazole byproducts can be efficiently inhibited.
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