Synthesis of 2-pyridones by cycloreversion of [2.2.2]- bicycloalkene diketopiperazines.
A general strategy for the conversion of [2.2.2]-diazabicyclic alkene structures to 2-pyridone aromatic heterocyclic products is reported. The reaction sequence starts from 2,5-diketopiperazine (DKP) derivatives, is compatible with both aromatic and aliphatic aldehyde components, and can intercept either intra- or intermolecular cycloaddition manifolds. Priming of one aza-bridging function in the intermediate [2.2.2]-DKP scaffold permits cycloreversion (microwave heating) and selective extrusion of cyanate derivatives leading to the formation of 2-pyridone structures. Progress toward the synthesis of louisianin A and B, antiproliferative 2-pyridone natural products, is also disclosed.
Department of Chemistry, The College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
Kaila A
KA
Margrey
Amy D
AD
Hazzard
Jonathan R
JR
Scheerer