An Azomethine Ylide Approach to Complex Alkaloid-like Heterocycles
| Autor: | Ignatius J. Turchi, Amy Maden, William V. Murray, David Francois |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Thiosemicarbazones
chemistry.chemical_classification Molecular Structure Intramolecular reaction Organic Chemistry Azomethine ylide General Medicine Heterocyclic Compounds 4 or More Rings Medicinal chemistry Toluene Cycloaddition Amino acid Nitrone Acetic acid chemistry.chemical_compound Alkaloids chemistry Intramolecular force Organic chemistry Pyrroles Azo Compounds Pyrrole |
| Zdroj: | The Journal of Organic Chemistry. 72:3097-3099 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo062579a |
| Popis: | The nitrone above is readily available via the intramolecular aza Diels−Alder reaction of an amino acid derived triene in acetic acid. Subsequent treatment of the nitrone in refluxing toluene with substituted actetylenes produced the pictured pyrrole. At lower temperatures a 2,3-dihydroisoxazole, which is the product of a 3 + 2 dipolar cycloaddition, is produced. Upon heating in refluxing toluene the 2,3-dihydroisoxazole is converted to the pyrrole. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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