Tunable Pd-Catalyzed Cyclization of Indole-2-carboxylic Acid Allenamides: Carboamination vs Microwave-Assisted Hydroamination
| Autor: | Egle M. Beccalli, Gianluigi Broggini, Gaetano Zecchi, Alice Bernasconi, Elena Borsini, Micol Rigamonti |
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| Rok vydání: | 2010 |
| Předmět: |
Indole test
Indoles Molecular Structure Intramolecular reaction Allene Aryl Organic Chemistry Carboxylic Acids chemistry.chemical_element Stereoisomerism Amides Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Nucleophile Cyclization Organic chemistry Hydroamination Microwaves Palladium Amination |
| Zdroj: | The Journal of Organic Chemistry. 75:6923-6932 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo101501u |
| Popis: | A variety of 3-vinyl-substituted imidazo[1,5-a]indole derivatives were synthesized by intramolecular Pd-catalyzed cyclization of the title allenamides through either a domino carbopalladation/exo-cyclization process or a novel hydroamination reaction that proceeds smoothly under microwave irradiation. Both the observed pathways involve a π-allyl-palladium(II) complex arising from insertion of the allene group into a palladium(II) species, the latter being formed in situ by the intervention of an aryl iodide or of the N-H group. In both cases, the role of nucleophile is covered by the indole nitrogen. |
| Databáze: | OpenAIRE |
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