A novel green synthesis of alpha/beta-amino acid functionalized pyrimidinone peptidomimetics using triazole ligation through click-multi-component reactions

作者：Balan Biny; Bahulayan D^*

来源：Tetrahedron Letters, 2014, 55(1): 227-231.

DOI：10.1016/j.tetlet.2013.11.002

• Solvent free synthesis
• Multi-component reactions
• Dihydropyrimidinones
• Click chemistry
• 1,2,3-Triazole

An innovative synthetic pathway for the preparation of a new series of triazole-decorated dihydropyrimidinone peptidomimetics with skeletal a or p-amino acid residue is reported. The protocol involves two synthetic steps with an initial solvent-free and catalyst-free synthesis of propargylated dihydropyrimidinone precursors using Biginelli condensations. The subsequent cycloaddition reactions of pyrimidinone alkynes with small peptide like azides prepared from Ugi or alternate Mannich type multicomponent reactions afforded the triazole decorated pyrimidinone peptide conjugates in excellent yield with high regio and stereospecificities. In total, a scaffold diversity contains II new pyrimidinone alkynes and 18 new pyrimidinone peptidomimetics were introduced into the chemical space.

• 出版日期2014-1-1