Synthesis of new steroid-β-lactam hybrids via palladium-catalyzed aminocarbonylation

Steroid-β-lactam and steroid-β-lactam-ferrocene conjugates were synthesized via palladium-catalyzed carbonylation of steroidal 17-iodo-16-enes in the presence of 3-amino-azetidin-2-ones. β-Lactam derivatives have been used for the first time as nucleophiles in the aminocarbonylation reaction. The products were obtained in good yields and were characterized by 1H and 13C NMR, IR and HRMS.

Graphical abstractPalladium-catalyzed aminocarbonylation was proved to be a useful tool for the functionalization of the β-lactam ring of 3-amino-β-lactams. By this methodology, new steroid β-lactam and steroid β-lactam-ferrocene hybrids were obtained in good yield. The products were characterized with various spectroscopic methods.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel steroid β-lactam and steroid β-lactam-ferrocene hybrids were produced by palladium-catalyzed carbonylation. ► Amino-β-lactams were used for the first time as nucleophilic reagents. ► All new compounds were fully characterized by 1H and 13C NMR, IR and HRMS.