Aza-Claisen Rearrangement in the Cyclization Reactions of Nitrogen-Containing Enynes via Ruthenium Vinylidene Complexes
| Autor: | Yi-Hong Liu, Yu Wang, Pei-Yun Chiang, Ying-Chih Lin |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Indole test
chemistry.chemical_classification Ligand Stereochemistry Organic Chemistry chemistry.chemical_element Aromatic amine Medicinal chemistry Catalysis Ruthenium Inorganic Chemistry Claisen rearrangement chemistry.chemical_compound chemistry Reagent Physical and Theoretical Chemistry Triphenylphosphine |
| Zdroj: | Organometallics. 29:5776-5782 |
| ISSN: | 1520-6041 0276-7333 |
| DOI: | 10.1021/om100292d |
| Popis: | The cyclization reaction of several diallyl aromatic amine molecules, each containing an ethynyl group at the ortho position of the aromatic ring, is accompanied by an aza-Claisen rearrangement, causing an allyl group migration to give substituted indole compounds. This cyclization is catalyzed by ruthenium triphenylphosphine and diphenylphosphinoethane (dppe) complexes as well as gold complexes with silver reagent. The less sterically crowded dppe complex is a more efficient catalyst. The mechanism involving a vinylidene intermediate is proposed on the basis of isolation of several intermediates in the ruthenium-catalyzed system. Single crystals of a metal complex with the cyclized ligand were obtained, and the structure was determined by an X-ray diffraction analysis. |
| Databáze: | OpenAIRE |
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