Synthesis of new analogs of N-substituted(benzoylamino)-1,2,3,6-tetrahydropyridines

Abstract

The tetrahydropyridine (THP) moiety is notably present in synthetic and natural products, playing a cardinal role in the food, cosmetic, and pharmaceutical industries. The THP structure is an instrumental constituent and is widely found in alkaloids that have therapeutic properties against inflammation, cancer, the nervous system, and bacterial infections. The use of THPs has gained traction, so it is imperative to increase the structural database through the synthesis of THP derivatives. The focus of this study is to make structural modifications to the benzene ring portion of the lead compound while keeping the pyridine ring constant. Eleven novel THP analogs were synthesized using a four-step synthetic approach involving partial reduction of N-substituted ylides into 1,2,3,6-THPs. The results illustrate that 11 THPs were successfully synthesized in low to moderate yields. Flash chromatography was utilized for purification. Proton nuclear magnetic resonance, deuterium oxide exchange, carbon nuclear magnetic resonance, infrared spectroscopy, and CHN elemental analysis were utilized to characterize the THP analogs. This study aids in contributing knowledge to the THP database.

Keywords

• synthesis
• tetrahydropyridines
• ylides
• partial reduction