Synthesis Of 3-(arylmethylene)-2,3-dihydro-4-quinolinone Catalyzed By TfOH

The 3-substituted 2,3-dihydro-4-quinolinone is an important skeleton in medical drugs and an important intermediate in organic synthesis.How to construct such a skeleton efficiently and simply and use it as an intermediate for further transformation research has become a very challenging and valuable work.Based on the reports of known literature and the previous research of the research group,a one-pot synthesis method of3-arylmethylene-2,3-dihydro-4-quinolinone catalyzed by Tf OH was developed in this paper.In this paper,under the conditions of Tf OH catalysis,nitrogen-protected o-propynol-aniline compounds are used as substrates to achieve 3-(aromatics)by tandem Meyer-Schuster rearrangement,intramolecular conjugate addition and aldol condensation reaction.One-pot synthesis of(methylidene)-1-p-toluenesulfonyl-2,3-dihydro-4-quinolinone.The reaction has the characteristics of simple experimental operation,high atomic utilization rate,high yield,and wide range of substrates.In addition,the catalyst used does not contain heavy metals,and only the target compound of 3-arylmethylene-2,3-dihydro-4-quinolinone and water are generated in the reaction,which has no impact on the environment and is a green synthesis method.More than twenty new compounds were synthesized by this method,and the fluorescence emission intensities of several of them were preliminary studied.At the same time,no synthetic literature has been reported on this synthetic route.