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Diastereoselective, multicomponent access to trans-2-aryl-4-arylamino-1,2,3,4-tetrahydroquinolines via an AA'BC sequential four-component reaction and their application to 2-arylquinoline synthesis.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2013 Jan 28; Vol. 11 (4), pp. 569-79. Date of Electronic Publication: 2012 Oct 22. - Publication Year :
- 2013
-
Abstract
- 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 FeCl(3) in methanol.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 11
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 23090014
- Full Text :
- https://doi.org/10.1039/c2ob26754c