The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens
| Autor: | E. I. Lazhko, Ilyia I. Rozhkov, L. N. Yudina, Alexander M. Korolev, Maria N. Preobrazhenskaya, Yury N. Luzikov, Ludmila N. Lysenkova |
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| Rok vydání: | 2001 |
| Předmět: |
Cyclopentenone
Hot Temperature Indoles Molecular Structure Chemistry Hydrolysis Organic Chemistry Molecular Conformation Ascorbic Acid Cyclopentanes General Medicine Ascorbic acid Biochemistry Analytical Chemistry chemistry.chemical_compound Ascorbigen Cascade reaction Organic chemistry Hydroxymethyl Nuclear Magnetic Resonance Biomolecular Enone |
| Zdroj: | Carbohydrate Research. 330:469-477 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(00)00310-4 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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