The Study On The Synthesis Of 2-Phenyltetrahydropyridine Derivatives And Its N-Ylide’s Rearrangement Reaction

2-Phenyltetrahydropyridine is an important pharmaceutically active fragment in medicine for nervous diseases.Efficient and simple synthesis of 2-phenyltetrahydropyridine derivatives has become one of the attractive research topics.This article summarizes the synthesis methods of 2-phenyltetrahydropyridine and the research progress of Stevens rearrangement induced by ammonium ylide.Based on the previous research,we developed a method for synthesis of 2-phenyltetrahydropyridine by using(phenylmethylene)dicarbamate derivatives and isoprene as starting materials.On this basis,we reduced cycloaddition products and reacted with bromoacetonitrile,2-bromoacetophenone,and ethyl bromoacetate to form quaternary ammonium salts.Then we investigated its chemical behavior reaerrangement reaction.We studied the selectivity of the rearrangement reaction in the presence of allyl group and benzyl group at the same time.Seven-membered ring products generated by [1,2] rearrangement,five-membered ring products generated by [2,3] rearrangement,and products generated by Hofmann elimination reaction were obtained,which provide compound reserves for subsequent medicinal chemistry research.After that,a preliminary screening of 2-phenyltetrahydropyridine and its derivatives was performed for cytotoxicity,and it was found the compounds have good inhibitory effect on U2 OS,HepG2 and T47 D cells.