199435-31-9Relevant articles and documents
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
Ribelles, Pascual,Sridharan, Vellaisamy,Villacampa, Mercedes,Ramos, M. Teresa,Menéndez, J. Carlos
, p. 569 - 579 (2013/02/26)
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.
Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization
Hennessy, Edward J.,Buchwald, Stephen L.
, p. 12084 - 12085 (2007/10/03)
A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright
