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Issue 4, 2013
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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

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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 FeCl3 in methanol.

Graphical abstract: 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

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Publication details

The article was received on 06 Sep 2012, accepted on 03 Oct 2012 and first published on 05 Oct 2012


Article type: Paper
DOI: 10.1039/C2OB26754C
Org. Biomol. Chem., 2013,11, 569-579

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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

    P. Ribelles, V. Sridharan, M. Villacampa, M. T. Ramos and J. C. Menéndez, Org. Biomol. Chem., 2013, 11, 569
    DOI: 10.1039/C2OB26754C

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