Addition Of Acetvlenic Ketones And Its Application In The Synthesis Of Polvsubstituted Oleifns And Cyclic Compounds

In this thesis, the addition reaction of acetylenic ketones was studiedand a series of functionalized polysubstituted olefins and chromenone orbenzofuranone were synthesized. The thesis consists of the following twoparts:Firstly, we studied the synthesis of iodo-substituted vinyl ethers byCu(OTf)2-catalyzed addition reaction of acetylenic ketones.Functionalized polysubstituted alkenes——carbonyl-and iodo-containedvinyl ethers were synthesized by Cu(OTf)2-catalyzed one-pot reaction ofacetylenic ketones, alcohols and I2-PhI(OAc)2. The reaction has highregio-and stereoselectivity. All products were characterized by1H NMR,13C NMR, IR and HRMS. The molecular structures of compounds(Z)-2-iodo-3-methoxy-3-phenyl-1-p-tolylprop-2-en-1-one(3a) and(Z)-3-ethoxy-2-iodo-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (3l)were confirmed by X-ray diffraction analysis.Secondly, we studied the synthesis of benzohetero cycliccompounds containing oxegen atom by intramolecular addition reactionof acetylenic ketones. PBu3-catalyzed intramolecular addition ofacetylenic ketones containing nucleophilic phenolic hydroxyl wasinvestigated. The results show that chromenone or benzofuranone wasobtained respectively with the different substituents of acetylenic ketones.All products were characterized by1H NMR,13C NMR, IR and HRMS.The molecular structure of compound (Z)-2-(4-methylbenzylidene)-benzofuran-3(2H)-one (5b) was determined by X-ray diffraction analysis.The research results provided a new method to synthesizepolysubstituted olefins and chromenone or benzofuranone compounds.The method has the advantages of easily available starting materials and simple operation. The further transformation of these compounds waspossible because of the existence of carbonyl and iodo functional groups.