Tetrahedron Letters

Efficient copper-catalyzed intramolecular N-arylation for the synthesis of oxindoles

YH Jhan, TW Kang, JC Hsieh

Index: Jhan, Yu-Huei; Kang, Ting-Wei; Hsieh, Jen-Chieh Tetrahedron Letters, 2013 , vol. 54, # 9 p. 1155 - 1159

Full Text: HTML

Citation Number: 12

Abstract

An efficient copper-catalyzed intramolecular N-arylation was performed by using substituted 2-(2-bromoaryl) acetamide with a small amount of Cu2O and benzene-1, 2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields of oxindoles with tolerance of a wide variety of substrates.

~89%

~81%

~45%

~74%

~99%

~98%

~88%

~72%

~92%

Two new stereochemically complementary oxindole synthesis

[Fleming, Ian; Loreto, Maria Antonietta; Michael, Joseph P.; Wallace, Ian H. M. Tetrahedron Letters, 1982 , vol. 23, # 19 p. 2053 - 2056]

Conformationally Constrained ortho-Anilino Diaryl Ureas: Dis...

[Qiao, Jennifer X.; Wang, Tammy C.; Ruel, Rejean; Thibeault, Carl; L'Heureux, Alexandre; Schumacher, William A.; Spronk, Steven A.; Hiebert, Sheldon; Bouthillier, Gilles; Lloyd, John; Pi, Zulan; Schnur, Dora M.; Abell, Lynn M.; Hua, Ji; Price, Laura A.; Liu, Eddie; Wu, Qimin; Steinbacher, Thomas E.; Bostwick, Jeffrey S.; Chang, Ming; Zheng, Joanna; Gao, Qi; Ma, Baoqing; McDonnell, Patricia A.; Huang, Christine S.; Rehfuss, Robert; Wexler, Ruth R.; Lam, Patrick Y. S. Journal of Medicinal Chemistry, 2013 , vol. 56, # 22 p. 9275 - 9295]