The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-cyclopent-2-enone derivatives from ascorbigens |
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Authors: | Korolev A M Yudina L N Rozhkov I I Lysenkova L N Lazhko E I Luzikov Y N Preobrazhenskaya M N |
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Institution: | Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow. |
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Abstract: | A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. |
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Keywords: | Ascorbigen -Ascorbic acid 2-Hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone |
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