Synthesis of 4-amino-1,2,3,4-tetrahydropyridine derivatives by intramolecular nucleophilic addition of tertiary enamides to in-situ generated imines
The reactivity of stable tertiary enamides in nucleophilic addition reaction with various in-situ generated imines was explored. Under very mild conditions, formyl-bearing tertiary enamides reacted with both aromatic and aliphatic amines to form imine intermediates. In the absence or presence of p-toluenesulfonic acid as a catalyst, intramolecular nucleophilic addition of enamide to imine functionality proceeded effectively to produce diverse 4-amino-1,2,3,4-tetrahydropyridine derivatives in good to excellent yields.
Keywords: Chiral Bronsted Acid ; 3-Component Povarov Reaction ; Clausena-Alkaloids ; Highly Efficient ; Enantioselective Synthesis ; Cgp 49823 ; 4-Aminopiperidines ; Piperidines ; Cyclization ; Antagonists
Record created on 2012-10-01, modified on 2016-08-09