Lewis-Acid-Catalyzed Three-Component Reaction Of Secondary Amide-Aldehyde-Alkene For The Synthesis Of Allylamine Derivatives

Allylamines are of great importance in organic synthesis. They are found in a wide variety of bioactive natural products, and are valuable intermediates to a range of products such as alkaloids, amino acids, etc. In addition to effects in pharmacology, allylamine compounds have play important roles in chemistry synthesis. This paper reviews the recent advances in the synthesis of allylamines, and studied I2 or trifluoromethanesulfonate promoted three-component reaction of electron-poor N-heterocycles, N- methyl-benzenesulfonamide or thiocaprolactam with aldehydes, unactivated alkenes for allylamines. This paper can be summarized as following:1. I2-catalyzed three-component reaction of N-heterocycles and Nmethyl-benzenesulfonamide, paraformaldehyde and ethyl glyoxylate with terminal olefins allows for clean generation of N-allylic substituted N-heterocycle and Nmethyl-benzenesulfonamide derivatives. The compounds were confirmed by IR, 1H NMR, 13 C NMR, HRMS. The utility of this method was also demonstrated by the rapid synthesis of Naftifine motif from N-methyl-1-naphthamide, paraformaldehyde, and styrene in one-pot manner.2. Bi(OTf)3 or I2/Fe(OTf)3-catalyzed three-component reaction of N-heterocycles and N-methyl-benzenesulfonamide, paraformaldehyde and ethyl glyoxylate with terminal olefins allows for allylamine derivatives in higher yield. I2/TfOH-catalyzed three-component condensation reaction of thio caprolactam with paraformaldehyde, substituted styrene allows for allylamine derivatives. The compounds were confirmed by IR, 1H NMR, 13 C NMR, HRMS. This process provides an efficient synthetic method to build allylamine unit.