Gold-Catalyzed Cyclisation by 1,4-Dioxidation

被引：21

作者：

Claus, Vanessa ^{[1
]}

Molinari, Lise ^{[1
]}

Buellmann, Simon ^{[1
]}

Thusek, Jean ^{[1
]}

Rudolph, Matthias ^{[1
]}

Rominger, Frank ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 40期

关键词：

cyclization; diphenylsulfoxide; diynes; gold; ynamides; TOPOISOMERASE-I; C-H; OXIDATIVE CYCLIZATION; INDENONE SYNTHESIS; BOND-CLEAVAGE; ALKYNES; GENERATION; ANNULATION; ACCESS; OPPORTUNITIES;

D O I：

10.1002/chem.201900996

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.

引用

页码：9385 / 9389

页数：5

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