The Effective oxidant H2O2 for the Doebner-Miller Syntheses of.docVIP

The Effective oxidant H2O2 for the Doebner-Miller Syntheses of 2, 3-dialkylquinoline via a one-pot reaction of aniline and aldehyde Abstract A convenient and efficient synthesis of substituted quinolines via a simple one-pot reaction of an aniline and aldehyde in the presence of the general Lewis acid AlCl3 and oxidant H2O2 (hydrogen peroxide) was developed. The effect of the oxidant on the yield and selectivity of quinoline derivaties was studied, and the experimental results expressed that when the molar ratio of aniline, aldehyde, and oxidant was 1: 3: 0.5 at 25 oC, the yield of quinoline was improved actually compared to the H2O2 was absent, also the reaction time was reduced obviously. As expected, the side product N-alkylaniline was not found, either. Which showed that the selectivity of qunolines was almost 100%. Moreover, the substituent effect was also investigated. Key words：Oxidant (H2O2) Effect, Doebner-Miller synthesis, Quinoline derivatives Introduction It is more then one hundred years since the quinolines and their derivaties were explored, which were used for many drugs and agricultural chemicals because of the excellent biological and pharmaceutical properties. As these years, the applications of quinolines extend to antioxidant in synthetic rubber and biology1a-c, metal ions detection in Environmental2a-b, biological science3a-b, and thermally stable transparent materials of electronics, optoelectronics and nonlinear optics4. Thus, the synthesis of quinoline derivatives always has been one of hotspots of chemical research. So far, chemists have explored various ways to synthesize of quinolines, and most of them were the modifications of the traditional methods, for example, Doebner-Miller5a-c, Skraup6a-d and Friedl?nder7a-e syntheses, which were generally considered to be the most versatile methods of synthesis of quinolines. However, many of the methods suffer from harsh reaction conditions5c, 8a-b or consist of multiple steps9a-e. Moreover,