3299-44-3Relevant articles and documents
Reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate: An easy access to 2,3-dialkylquinolines
Ali, Saghir,Gattu, Radhakrishna,Singh, Varun,Mondal, Santa,Khan, Abu T.,Dubey, Gurudutt,Bharatam
, p. 1785 - 1793 (2020/03/17)
We report the reaction behaviour of arylamines with nitroalkenes in the presence of bismuth(iii) triflate (10 mol%) and diacetoxyiodobenzene (10 mol%). We obtained 2,3-dialkylquinoline derivatives instead of the expected 3-alkylindole derivatives. The present reaction is an alternative approach for the synthesis of 2,3-dialkylquinoline derivatives under milder conditions. Furthermore, we establish the mechanistic pathway by theoretical calculations using Gaussian 09 software [B3LYP/6-311+G(d,p)], which shows that the conventional aza-Michael reaction is preferred over Michael addition. Aliphatic nitroalkenes behave in a different manner than aromatic nitroalkenes. An aza-Michael adduct gives rise to an imine by the elimination of water which may tautomerize to the corresponding enamine. The resulting imine and enamine intermediates react together to afford the desired quinoline derivatives. This protocol has the advantages of consecutive formation of one C-N and two C-C bonds, high regioselectivity, broad substrate-scope and good yields.
Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines
Cho, Chan Sik,Oh, Byoung Ho,Kim, Joon Seok,Kim, Tae-Jeong,Shim, Sang Chul
, p. 1885 - 1886 (2007/10/03)
Anilines react with an array of trialkylamines in the presence of a catalytic amount of RuCl3*nH2O and bis(diphenylphosphino)methane together with SnCl2*2H2O and hex-1-ene as hydrogen acceptor in dioxane at 180 deg C to afford the corresponding 2,3-disubstituted quinolines in moderate to good yields.
