Base-Promoted Synthesis of 3-Alkenyl-2-pyridones from N-Propargyl-β-enaminones and Aryl Aldehydes

Main observation and conclusion In this article, we report a base-promoted sequential cyclization/aldol-type condensation/isomerization cascade reaction of N-propargyl-beta-enaminones with aryl aldehydes. The key step in this protocol is the generation of 1,4-oxazepine anions from N-propargyl-beta-enaminones under basic conditions, which are captured by aryl aldehydes. The method allows the formation of one pyridone core and one C-C double bond in one pot, and the preparation of a variety of densely decorated pyridone derivatives in moderate to good yields with broad functional group tolerance.

Automated summary

This article presents a base-promoted sequential reaction of N-propargyl-beta-enaminones with aryl aldehydes, allowing the synthesis of densely decorated pyridone derivatives in moderate to good yields with broad functional group tolerance in one pot.