Palladium(II)/Copper Halide/Solvent Combination for Selective Intramolecular Domino Reactions of Indolecarboxylic Acid Allylamides: An Unprecedented Arylation/Esterification Sequence
| Autor: | Elena Borsini, Simona Galli, Egle M. Beccalli, Vincenzina Barbera, Giuseppe Lanza, Gaetano Zecchi, Gianluigi Broggini |
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| Rok vydání: | 2012 |
| Předmět: |
Indole test
Chemistry domino reactions chemistry.chemical_element Halogenation Homogeneous catalysis General Chemistry palladium homogeneous catalysis Medicinal chemistry palladium(II)/copper copper chemistry.chemical_compound Nucleophile Intramolecular force Organic chemistry Acetonitrile Acyl group Palladium |
| Zdroj: | Advanced Synthesis & Catalysis. 354:159-170 |
| ISSN: | 1615-4169 1615-4150 |
| DOI: | 10.1002/adsc.201100614 |
| Popis: | Intramolecular oxidative palladium-catalyzed reactions of indolylallylamides in the presence of the couple bis(acetonitrile) palladium dichloride and copper(II) halide are described. Starting from 2- and 3-indolylallylamides and involving in both cases the C-3 position of the indole nucleus, variously substituted β-carbolinones were obtained by arylation/halogenation, arylation/esterification or arylation/carboalkoxylation processes. On the other hand, an unusual aminohalogenation/halogenation sequence performed on 2-indolylallylamides gave rise to pyrazino[1,2-a]indole products. The carboesterification process is the result of an unknown path that involves the DMF or DMA used as solvent. The outcome of the reactions of the 3-indolylallylamides arises from a totally selective 1,2-migration of the acyl group on the supposed spiro intermediates formed from the nucleophilic attack of the C-3 indole position. |
| Databáze: | OpenAIRE |
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