Halogen-Radical-Promoted Dearomative Aza-Spirocyclization of Alkynylimines: An Efficient Approach to 3-Halo-Spirocyclohexadienones

Dianpeng Chen; Jianming Li; Yingying Shan; Peiying Cui; Yutong Zhao; Laijin Tian; Guanyinsheng Qiu

doi:10.1055/s-0039-1690746

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(04): 609-618
DOI: 10.1055/s-0039-1690746

paper

Halogen-Radical-Promoted Dearomative Aza-Spirocyclization of Alkynylimines: An Efficient Approach to 3-Halo-Spirocyclohexadienones

Dianpeng Chen∗

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Jianming Li

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Yingying Shan∗

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Peiying Cui

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Yutong Zhao

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Laijin Tian

^aChemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, P. R. of China eMail: chendp@zju.edu.cn eMail: shanyying@zju.edu.cn

,

Guanyinsheng Qiu ∗

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, P. R. of China eMail: qiuguanyinsheng@mail.zjxu.edu.cn

^cSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Hunan 411201, P. R. of China

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Abstract

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Abstract

A novel halogen-radical-promoted dearomative aza-spirocyclization of alkynylimines for the synthesis of 3-halo-spirocyclohexadienones is described. In this process, it is believed that a radical addition, 5-exo-trig cyclization, and dearomative aza-spirocyclization are involved. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.

Key words

halogen radical - dearomative aza-spirocyclization - alkynylimine - 3-halo-spirocyclohexadienone - 5-exo-trig cyclization

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