Iodine-catalyzed The Synthesis Of N-3 Allyl Quinazoline-2,5-diones Allylamine Derivatives And Study On The Isomerization Reaction Of Allylamine

Allyl amine compounds are of great important biological activities, it is also a kind of most valuable synthetic organic intermediates to a range of important bioactive compounds such as lactam, quinoline and indole, alkaloids, amino acids. In addition, allyl amine compounds can be used as the substrate in many reactions, such as the synthesis of chiral compounds, the intramolecular isomerization of allyl and rearrangement reaction which can obtian some new valuable products.In consideration of the important research value, the synthesis of allylamine compounds and the reaction research of its derivatives has aroused a lot of strong interests in many groups. In this thesis, we studied molecular iodine catalyzed three components reaction of 4-aryl-7,7-dimethyl-1,2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione, aldehydes and endmost olefin synthesis of N-3 allyl substituted quinazoline-2,5-dione derivatives. At the same time,Palladium acetate catalyzed the isomerization reaction of N-3 allyl substituted 3,4-dihydropyrimidinones compounds to synthesize N-3 propenyl substituted 3,4-dihydropyrimidinone derivatives.The main research contents and results were as following:1. We reviewed the recent advance in the synthesis of allylamine compounds and its derivatization reactions.2. The molecular iodine-catalyzed three-component reaction of octahydroquinazoline-2,5-diones with aldehydes(ethyl glyoxylate or paraformaldehyde) and styrenes provides a seize of N-allylic substituted octahydroquina-zoline-2,5-dione derivatives with high regioselectivity. And the compounds were confirmed by IR, 1H NMR, 13 C NMR and HRMS spectroscopic analysis.3. Using Palladium acetate as catalyst, Xanphos as ligand, Sodium tert-butoxide as base, under N2 protection, the N-3 propenyl substituted 3,4-dihydropyrimidinone derivatives were synthesized by the intramolecular isomerization reaction of N-3 allyl substituted 3,4-dihydropyrimidinones compounds. And the compounds were confirmed by 1H NMR, 13 C NMR and HRMS spectroscopic analysis.