Preliminary Study On Cascade Tandem Reaction Based On M-S Rearrangement Of 3-Arylpropargyl Alcohol

In this article,we studied the series reaction of the Meryer-Schuster rearrangement reaction based on aryl propargyl alcohol with the nucleophile Ts NH₂ and the electrophile chalcone.The research results show that 3-arylpropargyl alcohol has wide applicability as a raw material for M-S rearrangement to participate in the reaction.And then,after we optimized the reaction conditions of arylpropynol with Ts NH₂ and chalcone.We have conducted in-depth research on the universality of reaction substrates,and applied research on the reaction to a certain extent.Bi（OTf）₃-catalyed reaction of 3-aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated,which provided a facile route for the synthesis of a large variety ofα-halo-β-amino ketones.The key intermediates,β-amino ketones,were obtained through tandem Meyer-Schuster rearrangement reaction of propargyl alcohols and intermolecular Michael addition ofα,β-unsaturated ketones and sulfonamide.Then the in situ generatedα-halo-β-amino ketones underwent the base-promoted intramolecular cyclization to give diverse acyl aziridines in a one-pot procedure.These transformations are reliable on a large scale.The high yields and convenient experimental operations make it a valuable method for the construction ofα-halo-β-amino ketones and acyl aziridine derivatives.We then studied the reaction between aryl propargyl alcohol and the electrophile chalcone.The experimental results show that this is an efficient method for the synthesis of methyl ketone.In our experiment,we first obtained the important intermediate compound methyl ketone through the Meyer-Schuster rearrangement reaction and the Michael addition reaction of the discordant enone and the electrophilic chalcone.Next,an aryldiketone malononitrile compound is generated by a one-pot method of base-promoted methyl ketone and malononitrile.