Solid-Phase Synthesis of 3-Aminopyrrole-2,5-dicarboxylate Analogues
| Autor: | Yann Brouillette, William D. Lubell, Frederik J. R. Rombouts |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Salt (chemistry) General Chemistry Sodium methoxide Acylation Hydroxyproline Resins Synthetic chemistry.chemical_compound Solid-phase synthesis chemistry Bromide Alcohol oxidation Polymer chemistry Trichloroacetyl chloride Combinatorial Chemistry Techniques Organic chemistry Pyrroles Amines Pyrrole |
| Zdroj: | Journal of Combinatorial Chemistry. 8:117-126 |
| ISSN: | 1520-4774 1520-4766 |
| DOI: | 10.1021/cc0500912 |
| Popis: | An efficient strategy has been developed for the solid-phase parallel synthesis of 3-aminopyrrole-2,5-dicarboxylate analogues. A library of twenty-nine 2,3,5-trisubstituted pyrroles has been synthesized on Wang resin by a 5-6 step process. The attachment of (2S,4R)-4-hydroxy-N-(PhF)proline cesium salt (PhF = 9-(9-phenylfluorenyl)) to Wang bromide resin, followed by alcohol oxidation, produced the resin-bound 4-oxo-N-(PhF)prolinate as the pyrrole precursor. Resin-bound 3-aminopyrroles were synthesized by treatment of the oxo-N-(PhF)prolinate resin with different secondary amines and diversified at the 2-position by acylation with trichloroacetyl chloride and haloform reactions with primary amines. 3-Aminopyrrole-2,5-dicarboxylates were isolated in 81-99% purity and 51-99% yields after cleavage from the resin using TFA or sodium methoxide. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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