Aromatic C-H Bond Functionalized via Zwitterion Intermediates to Construct Bioxindole Containing Continuous
Li Niu1, Rou Pi1, Suzhen Dong1
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Chemical Engineering , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.
Abstract:
Both bioxindoles and continuous quaternary carbons play important roles in pharmaceutical scaffolds. However, few examples were developed to construct bioxindoles containing continuous quaternary carbons because of the steric hindrance effect. Here, a rhodium(II)-catalyzed three-component reaction of N,N-disubstituted anilines, 3-diazooxindoles, and isatin ketimines to deliver the 3-amino-3'-aryl-bioxindole compounds containing continuous quaternary carbons as products is developed. This transformation is proposed to proceed in a Mannich-type trapping of a zwitterion intermediate initiated from aromatic C-H bond functionalization. Several of these compounds exhibit good inhibitory activity against growth of osteosarcoma cell lines.
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