Synthesis of Substituted 2-Pyridones via 6?-Electrocyclization of Dienyl Isocyanates

A one-pot Curtius rearrangement of dienyl carbox-ylic acids followed by a 6 pi-electrocyclization process to formsubstituted 2-pyridone products has been developed. Dienylisocyanates generated from aliphatic acids were more reactivethan their aromatic counterparts. Additionally, substitutionpatterns of the carboxylic acids had an impact on the efficiencyof the cyclization.

Automated summary

A one-pot Curtius rearrangement followed by a 6 pi-electrocyclization process has been developed for the synthesis of substituted 2-pyridone products from dienyl carboxylic acids. The dienyl isocyanates generated from aliphatic acids showed higher reactivity compared to their aromatic counterparts, and the substitution patterns of the carboxylic acids influenced the efficiency of the cyclization.