Synthetic Communications p. 2574 - 2584 (2012)
Update date:2022-08-02
Topics:
Guo, Qiaoxia
Wang, Wennian
Teng, Weiling
Chen, Liwei
Wang, Yanqing
Shen, Baojian
(Chemical Equation Presented) A convenient one-pot method for the synthesis of substituted quinolines via the reaction of aniline and aldehyde in the presence of a Lewis acid (AlCl3) and an oxidant (H2O 2) has been developed. Hydrogen peroxide was found to promote the reaction by its function as a hydrogen hunter, hindering the formation of by-product N-alkylaniline. The effect of the oxidant on the yield and selectivity was studied. When the molar ratio of aniline, n-butyraldehyde, and H2O2 was 1:3:0.5 at 25°C, the yield of 3-ethyl-2-propylquinoline was improved from 64% (reaction without H 2O2) to 84% (with H2O2), and the quinoline selectivity was improved to almost 100%. Moreover, the reaction time was obviously reduced. The substituent effect was also investigated in this work. Copyright Taylor & Francis Group, LLC.
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