Facile construction of peptidomimetics by sequential C-S/C-N bond activation of Ugi-adducts

A novel selectively sequential C-S/C-N bond activation is presented. Through the combination of an Ugi-4CR and sequential C-S/C-N bond cleavage, diverse peptidomimetics containing a primary amide are prepared in a rapid, highly efficient and step-economical manner. This approach exhibits high yield, excellent chemoselectivity and functional group tolerance. Compounds derived from the pharmaceuticals febuxostat, probenecid and memantine as well as beta-amino acid are prepared. This method provides a new direction for the synthesis of peptidomimetics.