A Study On The Reactions Of Unsaturated Anilines Promoted By Triflic Acid

The research work mainly includes two parts, the first part is a mechanism research through the Friedel-Crafts alkylation reation of 2-allylic-aniline and benzene or toluene with the TfOH promoter; the second part show a research that the TFOH catalyzed a tandem Meyer-Schuster rearrangement/intramolecular hydroamination reaction process of o-anilinopropargy alcohols.The experimental work of the first part, the Friedel-Crafts alkylation reation of 2-allylic-aniline and benzene was initially studied with a number of acids as promoter, the TfOH was the best promoter, ? and ? products were obtained from the reaction, the ratio is between 4:1 and 5:1; the reation only got a product when it used toluene solvent. The Friedel-Crafts alkylation reation mechanism was explored through the experimental and. theoretical calculations. At present, the theoretical calculation is performing.In the second part, a novel and TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargy alcohols was developed, this transformation probably involved a tandem Meyer-Schuster rearrangement/intramolecular hydroamination reaction process. Studies on the protection groups of N atom and substitution groups in the phenyl ring exhibited that a general tandem reaction of Meyer-Schuster rearrangement and intramolecular hydroamination had been developed with good yield and a broad scope of reaction substrates.