Synthesis and structure of reaction products obtained from 1,2-epoxyperfluorobutane and bifunctional nucleophilic reagents |
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Authors: | Filyakova T I Kodess M I Slepukhin P A Zapevalov A Ya |
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Institution: | 1.Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, 620041, Russia ; |
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Abstract: | 1,2-Epoxyperfluorobutane readily reacts with bifunctional nucleophilic reagents to provide heterocyclic compounds with a pentafluoroethyl substituent. The reaction of this epoxide with thiourea and acetone thiosemicarbazone gave rise to 2-amino-5-pentafluoroethyl-5-fluoro-4(5H)-thiazolinone and 2-isopropylidenehydrazono-5-pentafluoroethyl-5-fluoro-4-thiazolidinone respectively. The reaction of 1,2-epoxyperfluorobutane with o-phenylenediamine and 2,3-diaminonaphthalene afforded in high yields 3-pentafluoroethyl-2(1H)-quinoxalinone and 3-(pentafluoroethyl)benzog]-2(1H)-quinoxalinone. The molecular and crystal structure of the obtained fluorine-containing heterocycles was established by XRD analysis. |
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