Assembly of 3-acyloxindoles via cui/L-proline-catalyzed intramolecular arylation of beta-keto amides.
[Structure: see text] Intramolecular coupling of beta-keto 2-iodoanilides catalyzed by CuI/L-proline in DMSO occurs at room temperature, affording substituted 3-acyloxindoles in good yield. Electronic effects on the aromatic ring have little influence on this reaction. Variations at the 1, 3, 4, 5, and 6 positions of the oxindoles were achieved by employing the corresponding amides.
Lu
Biao
B
Department of Chemistry, Fudan University, and State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai 200032, China.
Ma
Dawei
D
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*
D000577:Amides; D007211:Indoles; D011392:Proline