3299-44-3Relevant academic research and scientific papers
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 quinoline derivatives from anilines and aldehydes catalyzed by Cp2ZrCl2 and recyclable Cp2ZrCl2/MCM-41 system
Guo, Qiaoxia,Liao, Lijun,Teng, Weiling,Ren, Shenyong,Wang, Xiao,Lin, Yingying,Meng, Fanfang
, p. 117 - 122 (2016/02/03)
A facile method for the synthesis of quinoline derivatives using catalytic amount of Cp2ZrCl2 or Cp2ZrCl2 supported on MCM-41 (Cp2ZrCl2/MCM-41) in reaction of anilines and aldehydes is described. When Cp2ZrCl2/MCM-41 was used as catalyst, the yields of quinolines were enhanced by 5-15% compared with Cp2ZrCl2 as catalyst alone under the same reaction conditions. More importantly, Cp2ZrCl2/MCM-41 catalyst can be reused at least thrice by simple recover via filtration in air. Moreover, both Cp2ZrCl2 and Cp2ZrCl2/MCM-41 showed good catalytic activities to generate corresponding quinoline derivatives in moderate to good yields by varying the substituent of aniline and aldehyde. And the reaction conditions were optimized by studying the influences of reactant ratio, additives, solvent effect and reaction temperatures.
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.
