Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C-H Amidation.

Liang, Dongdong; Yu, Wenbo; Nguyen, Nam; Deschamps, Jeffrey R; Imler, Gregory H; Li, Yue; MacKerell, Alexander D; Jiang, Chao; Xue, Fengtian

Liang, Dongdong; Yu, Wenbo; Nguyen, Nam; Deschamps, Jeffrey R; Imler, Gregory H; Li, Yue; MacKerell, Alexander D; Jiang, Chao; Xue, Fengtian.

Afiliação

Liang D; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy , 20 Penn Street, Baltimore, Maryland 21201, United States.
Yu W; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy , 20 Penn Street, Baltimore, Maryland 21201, United States.
Nguyen N; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy , 20 Penn Street, Baltimore, Maryland 21201, United States.
Deschamps JR; Naval Research Laboratory , Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
Imler GH; Naval Research Laboratory , Code 6930, 4555 Overlook Avenue, Washington, D.C. 20375, United States.
Li Y; Department of Chemistry and Biochemistry, University of Maryland College Park , College Park, Maryland 20740, United States.
MacKerell AD; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy , 20 Penn Street, Baltimore, Maryland 21201, United States.
Jiang C; Department of Pharmaceutical Engineering, School of Chemical Engineering, Nanjing University of Science and Technology , Nanjing, Jiangsu 210094, China.
Xue F; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy , 20 Penn Street, Baltimore, Maryland 21201, United States.

J Org Chem ; 82(7): 3589-3596, 2017 04 07.

Article em En | MEDLINE | ID: mdl-28245353

RESUMO

We report a novel synthesis of phenanthridinones from N-methoxybenzamides using an oxidative C-H amidation reaction at room temperature in open air with modest to excellent yields. This method demonstrated unprecedented substrate scope. In particular, it solved the long-standing challenge in the synthesis of phenanthridinones with sterically demanding substitutions.

Assuntos

Amidas/química; Iodobenzenos/química; Fenantridinas/síntese química; Catálise; Estrutura Molecular; Oxirredução; Fenantridinas/química

Texto completo

Imprimir

XML

PubMed Links

Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fenantridinas / Amidas / Iodobenzenos Idioma: En Revista: J Org Chem Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Estados Unidos

Texto completo

Imprimir

XML

PubMed Links

Buscar no Google