The Structure-Reactivity-Chemoselectivity Relationship on the Reactions of 1-Unsubstituted Tautomeric 2-Pyridones with Benzyne

Article abstract of DOI:10.1246/bcsj.58.1149

The reactions of 2-pyridones with benzyne were investigated in order to gain some insight into the structure-reactivity-chemoselectivity relatinoship involved in the tautomeric systems.All reactions examined have resulted in the formation of Diels-Alder and Michael-type adducts.It has been shown that the Diels-Alder reactivities were well correlated with the HOMO energy levels of the 2-pyridone form and the yields of the Michael-type adduct were closely associated with the tautomeric equilibria.In summary, the chemoselectivities of 2-pyridones in the reaction with benzyne were largely affected by the tautomeric properties.