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

作者：Nag Somnath; Madapa Sudharshan; Batra Sanjay^*

来源：Synthesis, 2008, (1): 101-109.

DOI：10.1055/s-2007-990929

• Baylis-Hillman
• formamide
• N-formylation
• primary allyl amine
• 4(3H)-pyrimidinone
• 4-pyridinamine
• 2,3-dihydro-1H-pyrrolizin-1-one

The applications of the primary allylamines obtained from 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-dihydropyrrolizin-1-ones have been accomplished via treatment of allylamine with dimethoxyfuran followed by saponification and PPA-mediated intramolecular cyclization.

• 出版日期2008-1-3