Nucleophilic behavior of DBU in a conjugate addition reaction

Reaction of DBU with a diarylpyrone results in 1,4 addition of the DBU and subsequent fragmentation of the DBU moiety into an aminopropyl caprolactam. Incorporation of the fragmented DBU into the diarylpyridone is postulated to occur by an addition/elimination pathway. DBU reacts with pyrones 1 to g...

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Bibliographic Details
Published inTetrahedron letters Vol. 38; no. 40; pp. 7003 - 7006
Main Authors Johnson, Mary George, Foglesong, Robert J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.10.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENONES
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Summary:Reaction of DBU with a diarylpyrone results in 1,4 addition of the DBU and subsequent fragmentation of the DBU moiety into an aminopropyl caprolactam. Incorporation of the fragmented DBU into the diarylpyridone is postulated to occur by an addition/elimination pathway. DBU reacts with pyrones 1 to give unusual pyridones 2. Labeling studies indicate a novel mechanism via 3.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)01675-4