Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 4, Pages 569-579Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob26754c
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Funding
- MICINN [CTQ2009-12320-BQU]
- MINECO [CTQ2012-33272]
- UCM (Grupos de Investigacion) [GR35/10-A-920234]
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The CAN-catalyzed reaction between 3,5-disubstituted anilines, vinyl ethers and aromatic aldehydes leads to trans-2-aryl-4-arylaminotetrahydroquinolines, in an AA'BC sequential multicomponent transformation related to the Povarov reaction that was also extended to the use of a second aniline as the C-4 substituent. The unusual trans stereochemistry was explained by stabilization of the corresponding intermediate by intramolecular hydrogen bonding. The presence of the 4-anilino substituent allowed adapting the method to the synthesis of 4-unsubstituted 2-arylquinolines, by treatment of the crude product from the MCR with FeCl3 in methanol.
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