Ruthenium(II)-catalyzed [5 + 1] annulation reaction: a facile and efficient approach to construct 6-ethenyl phenanthridines utilizing a primary amine as a directing group

Jian Chen; Baolan Tang; Xuexin Liu; Guanghui Lv; Yuesen Shi; Tianle Huang; Huimin Xing; Xiaoyu Guo; Li Hai; Yong Wu

doi:10.1039/D0QO00769B

Ruthenium(ii)-catalyzed [5 + 1] annulation reaction: a facile and efficient approach to construct 6-ethenyl phenanthridines utilizing a primary amine as a directing group†

Jian Chen,‡^a Baolan Tang,‡^a Xuexin Liu,^a Guanghui Lv,^b Yuesen Shi,^a Tianle Huang,^a Huimin Xing,^a Xiaoyu Guo,^a Li Hai

*^a and Yong Wu

*^a

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* Corresponding authors

^a Key Laboratory of Drug Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17, 3th Section, South Renmin Road, Chengdu, P. R. China
E-mail: smile@scu.edu.cn, wyong@scu.edu.cn

^b Department of Pharmacy, Taihe Hospital, Hubei University of Medicine, No. 32 South Renmin Road, Shiyan, Huibei 442000, China

Abstract

A ruthenium(II)-catalyzed [5 + 1] annulation reaction between 2-arylanilines and cyclopropenones employing a free amine as a directing group has been developed. This protocol provides a facile and practical method for the preparation of a variety of biologically valuable 6-ethenyl phenanthridine scaffolds, and features the use of the cost-effective ruthenium catalyst, good functional group tolerance and no requirement of an external oxidant.

Organic Chemistry Frontiers

Ruthenium(ii)-catalyzed [5 + 1] annulation reaction: a facile and efficient approach to construct 6-ethenyl phenanthridines utilizing a primary amine as a directing group†

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Ruthenium(II)-catalyzed [5 + 1] annulation reaction: a facile and efficient approach to construct 6-ethenyl phenanthridines utilizing a primary amine as a directing group

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