Intermolecular Addition Of Allenamides

Allenamides are special classes of functionalized allenes,and important synthetic building blocks in modern organic synthesis.According to the structure characteristics of allenamides,the research work of this thesis has been focused on exploring the nucleophilic addition reaction of Allenamides with Aromatic heterocyclic compounds and sulfonamides.and the Electrophilic addition of allenamides and Halogenated reagent.Chapter 2: A catalyst-free intermolecular addition of indoles,pyrroles,and imidazole to allenamides is reported.The reaction proceeds smoothly at 80℃ and provides a series of(E)-ensulfonamide derivatives in high yields with excellent regioselectivity.enamides can also obtained when using acyl in place of tosyl as an amino-protecting group of allenamides.Chapter 3: A new method was developed to synthesize iodine-substituted Z-enamides through N-iodosuccinimide-mediated intermolecular iodofunctionalization of allenamides with indoles,pyrroles,and furans.These reactions proceed rapidly and tolerate a broad scope of substrates.The conjugated sulfimide ion species probably acts as the key intermediate.Chapter 4: An intermolecular iodoamination of allenamides with amines has been achieved under mild N-iodosuccinimide-mediated conditions delivering iodine-substituted allylamino Z-enamides in high regio-and stereoselectivity.These reactions proceed rapidly and tolerate a broad scope of substrates.Chapter 5: A strategy for the synthesis of 2-halo allylic aminal derivatives through regioselective 1,2-addition of allenamides with N-haloimides is presented.This reaction was conducted under very mild conditions and gave up to 99% yield.Moreover,the obtained halides allow functional group diversification by palladium-catalyzed coupling reactions,which could act as potential intermediates for the synthesis of valuable compounds.