Synthesis Of Alpha Amino Ketones And Their Application In Synthesis Of Pyrrole And Isoindolinone Compounds

Alpha amino ketones are important compounds which contain both amino and carbonyl functional groups in the same molecules. It is widely used in the field of organic synthesis because of its variety of unique chemical reactivity. In recent years, much attention has been paid to the application of alpha amino ketones. In this thesis, bromoacetophenone and arylamine were used as starting materials to obtain a-aminoketone. Then the solvent, base, catalyst conditions were controlled in order to afford pyrrole and isoindolinone compounds, and the main results were as follows:1. We found that a-aminoketone, terminal alkyne and tosyl azide were reacted in the role of catalyst, and then tosylacetamidine compounds were generated. The cyclization of these compounds via DBU and silica gel could give the multi-substituted pyrrole compounds in moderate yields in CH3CN(27-89%). 2. We developed a method for the synthesis of isoindolinones via the Pd-catalized cyclization of2-iodine benzamide compounds which were got by reaction of a-amino ketone and o-iodo-benzoyl chloride. Isoindolinones were obtained using i-PrOH as the solvent at70℃in moderate yields(58～96%).3. We found that cyclization of2-iodine benzamide could afford3-acyl isoindolinones at first, then they could be further coverted into3-hydroxyl isoindolinones under the condition of O2in moderate yields in i-PrOH at70℃(51-80%).