Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 26, Pages 7443-7465Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601823
Keywords
C-H activation; cobalt cycloaddition; heterocycles; N-H activation
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The reactivity of a range of pyridone and pyrazinone derivatives towards alkynes in the presence of cyclopentadienylcobaltbis(ethene) has been investigated. Depending on the nature of the substrates, [2+2+2]- or [2+2] cycloaddition, C-H, or N-H activation may occur. In the case of pyridones, the first three predominated with N-protected derivatives, whereas substrates containing N-H bonds followed an N-H activation pathway. The [2+2+2] cycloaddition of an N-buty-nylisoquinolone was applied successfully to the total synthesis of anhydrolycorinone. Pyrazinone substrates showed similar patterns of reactivity.
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