Transition Metal-Free N-S Bond Cleavage and C-N Bond Activation of Ugi-Adducts for Rapid Preparation of Primary Amides and & alpha;-Ketoamides

A novel method of transition metal-free N-S bond cleavage and subsequent C-N bond activation of Ugi-adducts was developed. Diverse primary amides and a-ketoamides were prepared in a rapid, step-economical and highly efficient manner in two steps. This strategy features excellent chemoselectivity, high yield and functional-group tolerance. Primary amides derived from the pharmaceuticals probenecid and febuxostat were prepared. This method opens a new pathway for the simultaneous synthesis of primary amides and a-ketoamides in an environmentally friendly manner.

Automated summary

A novel method was developed for transition metal-free N-S bond cleavage and subsequent C-N bond activation of Ugi-adducts. Diverse primary amides and a-ketoamides were prepared in a rapid, step-economic, and highly efficient manner in two steps. This strategy offers excellent chemoselectivity, high yield, and functional-group tolerance. Primary amides derived from the pharmaceuticals probenecid and febuxostat were successfully prepared. This method provides a new environmentally friendly pathway for the simultaneous synthesis of primary amides and a-ketoamides.