Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides

Deju Ye; Jinfang Wang; Xu Zhang; Yu Zhou; Xiao Ding; Enguang Feng; Haifeng Sun; Guannan Liu; Hualiang Jiang; Hong Liu

doi:10.1039/B904044G

Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides†

Deju Ye,^a Jinfang Wang,^a Xu Zhang,^ab Yu Zhou,^a Xiao Ding,^a Enguang Feng,^a Haifeng Sun,^a Guannan Liu,^a Hualiang Jiang^a and Hong Liu*^a

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* Corresponding authors

^a Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zu chong zhi Road, Shanghai, P. R. China
E-mail: hliu@mail.shcnc.ac.cn

^b Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong jia Xiang, Nanjing, P. R. China

Abstract

Using [Au(PPh₃)]Cl/Ag₂CO₃-catalyzed 5-endo-digcyclization in water under microwave irradiation, we developed a fast and green route to prepare indole-1-carboxamides from N′-substituted N-(2-alkynylphenyl)ureas. The described method is tolerant to a variety of functional groups, including N′-aryl, alkyl, heterocyclic, various N-(substituted-2-ethynylphenyl) and N-(2-ethynylpyridin-3-yl)ureas and affords moderate to high yields of the desired products.

Green Chemistry

Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides†

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Gold-catalyzed intramolecular hydroamination of terminal alkynes in aqueous media: efficient and regioselective synthesis of indole-1-carboxamides

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