Ruthenium-Catalyzed Oxidative Synthesis of N-(2-triazine)indoles by C-H Activation

Author:

Zeng Ming1ORCID,Chen Jiaqi1,Li Fengye1,Li Haojie1,Zhao Lan1,Jiang Dengzhao1,Dai Jun1,Liu Wenbo1

Affiliation:

1. School of Pharmacy and Life Science, Jiujiang University, Jiujiang 332005, China

Abstract

1,3,5 triazines, especially indole functionalized triazine derivatives, exhibit excellent activities, such as anti-tumor, antibacterial, and anti-inflammatory activities. Traditional methods for the synthesis of N-(2-triazine) indoles suffer from unstable materials and tedious operations. Transition-metal-catalyzed C-C/C-N coupling provides a powerful protocol for the synthesis of indoles by the C-H activation strategy. Here, we report the efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation from alkynes and various substituted triazine derivatives in a moderate to good yield, and all of the N-(2-triazine) indoles were characterized by 1H NMR, 13C NMR, and HRMS. This protocol can apply to the gram-scale synthesis of the N-(2-triazine) indole in a moderate yield. Moreover, the reaction is proposed to be performed via a six-membered ruthenacycle (II) intermediate, which suggests that the triazine ring could offer chelation assistance for the formation of N-(2-triazine) indoles.

Funder

Natural Science Foundation of Jiangxi province

Natural Science Foundation of China

Foundation of Jiangxi Provincial Department of Education

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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