Reactions of 5,6,7,8-tetrafluoro-4-hydroxycoumarin derivatives with benzylamine and aniline |
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Authors: | K V Shcherbakov Ya V Burgart V I Saloutin |
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Institution: | (1) I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi/Akademicheskaya, 620219 Ekaterinburg, Russian Federation |
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Abstract: | 5,6,7,8-Tetrafluoro-4-hydroxycoumarin reacted with benzylamine under mild conditions to give a stable salt, while its refluxing
with aniline or benzylamine in xylene afforded 5,6,7,8-tetrafluoro-4-phenyl(benzyl)aminocoumarins. Reactions of 3-acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins
with benzylamine followed different pathways, depending on the solvent. Condensation at the acyl substituent can be accompanied
by replacement of the F atom in position 7. 3-Acetylcoumarin formed a salt, while 3-acetimidoylcoumarin yielded a 7-monosubstituted
product. 3-Acetyl(acetimidoyl)-5,6,7,8-tetrafluoro-4-hydroxycoumarins reacted with aniline to give only 5,6,7,8-tetrafluoro-4-hydroxy-3-(N-phenylacetimidoyl)coumarin.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1170–1174, July, 2006. |
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Keywords: | coumarins amines organofluorine compounds nucleophilic substitution |
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