Study On The Synthesis Of N,2-allyl Aromatic Amines

N-Alkylation and Aza-rearrangement reactions are the two very importantorganic reactions. A lot of important organic intermediates, such as benzo-diazepine,benzo-indole derivatives were obtained through N-alkykation and Aza-rearrangementreactions. Therefore, which have wide application in organic synthesis. The reportedN-Alkylation and Aza-rearrangement reactions were mainly studied on saturatedhydro-carbons. However, contain unsaturated double bond in compounds ofN-Alkylation and Aza-rearrangement reactions are fewer reported, which need someof the harsh conditions of the precious metal catalyst, so that the application subjectto certain restrictions. Therefore, exploration and research alkylation andrearrangement reactions with unsaturated compounds will be of great significance. Inthis thesis, the synthesis and Aza-rearrangement reaction of N-allyl aromatic aminecompounds were reviewed compared with the method reported, this method has theadvantages of easy work-up, high yields and avoid the use of metal catalysts. Weobtained the optimum reaction conditions by studing the factors respectively whichaffect the reactions such as the reaction medium, temperature and time. Thestructures of all compounds were confirmed by IR,¹H NMR,¹³C NMR andElemental analysis.The thesis is mainly divided into four chapters:Chapter one:The progress of studies on the N-Alkylation and Aza-rearrangement reaction inthe organic synthesis in recent years. Especially the application and synthesis ofsingle-, dual-N-allyl aromatic amine compounds and derivatives, the Aza-rearrangement reaction of the N,N-diallyl aromatic amine compounds.Chapter two:A series of N-allyl aromatic amine compounds were synthesized by the reactionof aromatic amines and allyl bromide using water and THF as reaction solvent. Thismethod has the advantages of short time, high yields and the wide range ofapplications. Chapter three:An efficient method has been developed for the synthesis of N,N-diallylaromatic amine compounds by the reaction of aromatic amines and allyl bromideusing chloroform as reaction solvent. This protocol has the features of the short time,high yields, mild conditions, wide application and simple work-up.Chapter four:A various of N,N-diallyl aromatic amine compounds were synthesized viaAza-rearrangement reaction of N,N-diallyl aromatic amine compounds usinganhydrous aluminum chloride as catalyst in chlorobenzene.