Application of Primary Allylamine Derivatives of Baylis-Hillman Adducts to Heterocyclic Synthesis: Generation of 5-Benzyl-4(3H)-pyrimidinones and 2-Benzylidene-2,3-dihydropyrrolizin-1-ones

Abstract

The applications of the primary allyl amines afforded by the acetyl derivative of Baylis-Hillman adducts of acrylate for the synthesis of heterocycles using robust reactions are described. In the first strategy a one-pot synthesis of 5-benzyl-4(3H)- pyrimidinones have been achieved via N-formylation of the amines in the presence of neat formamide followed by ammonium formate-mediated cyclization. These pyrimidinones have been demonstrated to be excellent precursor to the 4-pyridinamine derivatives. In the second strategy the synthesis of 2-benzylidene- 2,3-dihydro-pyrrolizin-1-ones have been accomplished via treat- ment of allyl amine with dimethoxyfuran followed by saponifica- tion and PPA-mediated intramolecular cyclization.