Study On The Synthesis Of Pyrrolidine Compounds In Tandem Reaction

Heterocyclic compounds exist in numerous natural alkaloids that are one of the most important core in organic synthetic chemistry at present.Pyrrolidine compounds have high biological activity and act as the structural framework of drugs,are widely used in the medical field.Above our research direction and the progress at home and abroad,this article introduces the free radical cyclization of 1,6-enyne that based on different catalytic manifold.A series of disubstituted pyrrolidine compounds have been constructed.It mainly includes the following three parts:1.To deliver a range of selenium-containing heterocyclic derivatives,we use 1,6-enyne derived from terminal alkyne and diphenyl diselenide as the substrates,excitated with visible light,dry toluene as solvent.It overcomes the shortcomings of previous work.This method features mild conditions,high atom-economy and a very broad substrate scope.2.A selenylative cyclization reaction of 1,6-enynes is described.The transformation of diaryl diselenide and 1,6-enynes by visible light,dry toluene as solvent,obtains diversified pyrrolidine compouds.The reaction does not require any external oxidant/reductant or photocatalyst and shows good functional group capability.3.The synthesis of cyano-containing heterocycles uses 1,6-enynes and bromoacetonitrile as substrates,CuI as catalyst,1,10-phen as ligand,NaHCO3 as base in MeCN under a N2 atmosphere.The raection triggers the radical cyclization to obtain vinyl C-Br bond and nitrile group-containing heterocycles.The solution avoids using the transition metal catalyst and toxic reagent.The structures of compounds above are all characterized by HRMS,1 H NMR,13C NMR,I9F NMR and IR.The configuration of the products are confirmed by X-ray single crystal diffraction.