The Application Of 2-Bromobenxoyl Derivative And 2-iodobenxoyl Derivative In Synthesis Of 1H-inden-1-ones And Benzo[1,4] Diazepin-6(5h)-ones

The ideal organic synthesis can lead to novel and complex compound using simple,readily available substance as starting materials.Tandem reaction is an efficient approach for the synthesis of unique chemical structure with high stereoselectivity without isolating the intermediates.Thus much attention has been paid to the development and application of tandem reaction.Based on the concept of tandem reaction and the wide application prospect of indenones and benzodiazepines,in this dissertation we developed a way to access 1H-inden-1-ones and benzo[1,4]diazepin-6(5H)-ones using 2-bromobenxoyl derivative and 2-iodobenxoyl derivative respectively as the materials,and the whole work as follows:1.We developed the Pd-catalyzed Sonogashira coupling and carbopalladation between 1-(2-bromophenyl)-2-(phenylsulfonyl)ethanone and alkynes in moderate-to-good yields in THF at 60 ?(49-99%),featuring the regio-and stereoselective carbopalladation of the triple bond with Pd enolate species.2.We found a copper-catalyzed tandem reaction of 2-iodo-N-phenyl-N-(3-phenylprop-2-ynyl)benzamide with sodium azide in moderate yields in DMSO/H2O at 90 ?(32-72%).The reaction proceed via a[3+2]azide-alkyne cycloaddition and intramolecular Ullmann-type C-N coupling process,or C-N coupling and intramolecular[3+2]cycloaddition.