The Synthesis Of Allylamine Derivatives By Iodine-catalyzed Reaction Of Pyrimidinones/Amides, Paraformaldehyde And Substituted Styrenes

There are various kinds of organic compounds with nitrogen in natural and artificialmedicines. Allylamines are of great importance in organic synthesis. They are found in a widevariety of bioactive natural products, and are useful intermediates to a range of products suchas alkaloids, amino, etc. In addition to effects in pharmacology, allylamine compounds haveplay important roles in chemistry synthesis. In this thesis, we studied molecular iodinecatalyzed three-component reaction of3,4-dihydropyrimidinones or amide derivatives,paraformaldehyde with substituted styrenes giving a series of allylamine derivatives in highregioselectivitivies and good yields. This thesis can be summarized as following:1. We reviewed the recent advances in the synthesis of allylamines.2. The molecular iodine-catalyzed three-component reaction of3,4-dihydropyrimidinonederivatives, paraformaldehyde with substituted styrenes allows for clean generation ofN-allylic substituted3,4-dihydropyrimidinone derivatives in high regioselectivitivies. Thecompounds were confirmed by IR,1H NMR,13C NMR, HRMS, and the desired product werefurther confirmed by the X-ray crystal diffraction detection. A possible mechanism was alsoproposed.3. A multicomponent reaction of amides including cyclic amides and acyclic amides,paraformaldehyde and substituted styrenes was efficiently catalyzed by molecular iodine，producing a series of allylamine derivatives in a stereoselective way. The compounds wereconfirmed by IR,1H NMR,13C NMR, HRMS and so on. The reaction using electron-deficientN-phenylbenzamide gave a cyclization product as3,4-dihydroquinoline, suggesting acarbocation intermediate and an Aza-Prins cyclization/intramolecular Friedel Crafts reaction.