Abstract
The reaction of variously N-substituted α-furanamides with singlet oxygen has been examined. In addition to the expected fragmentation products the reaction affords rearranged 5-hydroxy- and 5-aryloxy-2(5H)-furanones. Products distribution depends on diverse factors: the presence of α-hydrogen, the presence of the amidic group, the nature and the number of nitrogen substituents. The rearrangement to 5-aryloxy-2(5H)-furanones is unreported.
Keywords: Photooxygenation, furanamides, furanones, N-O transfer, singlet oxygen, γ-Hydroxybutenolide.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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