Synthesis of 3,3-difluoro-2-oxindoles and larger sized rings
Many pharmaceuticals have fused ring systems and their bioactivity tends to increase with the introduction of fluorine containing functional groups. Currently known methods to create 3,3-difluoro-2-oxindole compounds have several significant drawbacks including the requirement of explosive materials, the use of over one equivalence of copper reagents, and inefficiency for formation of larger sized fused ring systems. For these reasons, we sought to discover reaction conditions that could create not only 3,3,-difluoro-2-oxindole systems, but expand into the syntheses of six, seven, and even eight membered fluorinated fused ring products. The novel Cu(I)-catalyzed reaction conditions are developed to form the desired five and seven membered rings effectively. Although the desired six and eight membered ring products were not formed, this thesis describes the interesting outcomes of these reactions as well.
Dai, Purdue University.
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