Aromatic C-H Bond Functionalized via Zwitterion Intermediates to Construct Bioxindole Containing Continuous Quaternary Carbons.
J Org Chem
; 84(23): 15192-15200, 2019 12 06.
Article
en En
| MEDLINE
| ID: mdl-31663338
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.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2019
Tipo del documento:
Article
País de afiliación:
China