Synthesis Of Polysubstituted Naphthylamines And Polysubstituted Benzo [a] Acridine Derivatives By Cyclization Reaction Of Enaminones

Enaminones are important pharmaceutical and chemical intermediates which are used to synthesis five-and six-membered heterocyclic compounds. Many novel chemical reactions can be achieved through the structure modification of enaminones and the design of reaction conditions. This thesis focused on the development of novel synthetic methodologies for cyclic compounds starting from enaminones.This paper mainly includes the following three parts:The first part:With the metal silver as catalyst, we realized the transformation from 2-alkynyl enaminones to a series of naphthyl amine derivatives successfully. The reaction first experienced deamination process of forming naphthalen-1(2H)-one intermediate which then underwent a condensation reaction with amines to give the desired product. This methodology offers rapid access to naphthyl amine derivatives, one of which was confirmed by X-ray single crystal diffraction. Twelve desired products were synthesized in moderate to good yields.The second part:With the metal iron as catalyst, we synthesized a series of benzo [a] acridine derivatives by cyclization of 2-alkenyl enaminones compound. One of benzo [a] acridine derivatives was confirmed by X-ray single crystal diffraction. This methodology offers rapid access to benzo [a] acridine derivatives. Twelve desired products were synthesized in moderate to good yields.The third part:The reaction condition from 1,3-butadiene derivatives to 1,3,5-triene derivatives was screened.All new compounds in this thesis were characterized by 1HNMR,13CNMR and MS spectroscopy.