Aza-michael Addition Reactions Of Indoles With 2-aroyl-1,3-diarylenones And Oxidative Coupling Reactions With 2-arylidenemalononitriles

The aza-Michael addition reaction is one of the most popular methods for forming carbon-nitrogen bonds,and it is also the concise method for preparing?-aminocarbonyl compounds.The aza-Michael reaction can be used to synthesize many fine chemicals,such as medicines and pesticides.The oxidative coupling reaction is generally a process in which C–C is formed by dehydrogenation of two C–H bonds under the catalysis of a transition metal and the oxidation of an oxidant.Therefore,the oxidative coupling reaction is also one of the routes to increase the carbon chain.Among them,there are several types of C–C coupling such as C(sp)–C(sp),C(sp~2)–C(sp~2),C(sp~3)–C(sp~3),C(sp~2)–C(sp~3)and so on.Oxidative coupling is widely used for the synthesis of chemicals used in agriculture,medicine,food,etc.Indole is a structural special chemical,which can not only undergo addition or coupling reactions at the C3 and C2 positions,but also can react at the N1 position.Indole and its derivatives are widely used in medicine,pesticides and food additives.Based on the above background,this thesis mainly studies the aza-Michael addition reactions of indoles with 2-aroylenones and the oxidative coupling reactions of indoles with 2-arylmethylenemalononitriles.Two series of indole-functionalized products are synthesized under mild conditions in high yields and high selectivity.Chapter 1:Some aza-Michael addition reactions and oxidative coupling reactions reported in recent years are reviewed.Some synthetic methods for indole and its derivatives,and some reactions using indole and its derivatives are also reviewed.Chapter 2:Twenty examples of 2-[((1H-indole-1-yl)(aryl)methyl]-1,3-diphenylpropan-1,3-diones were synthesized by aza-Michael addition of indoles with 2-aroylenones.The salient features of this protocol are no transition-metal catalysts,mild conditions,high chemical selectivity,high atom economy,high yields and simple work-up procedures.Chapter 3:The novel C(sp~2)–C(sp~2)bonds were constructed by aerobic oxidative cross-coupling of indoles and 2-arylmethylenemalononitriles.Various[(1H-indol-3-yl)(aryl)methylene]malononitriles were efficiently synthesized using air as an oxidant.The salient features of this protocol are no transition-metal catalysts,no organometallic reagents,high atom economy,high yields,mild conditions and simple work-up procedures.