Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones

Maozhong Miao; Huaping Xu; Yi Luo; Mengchao Jin; Zhengkai Chen; Jianfeng Xu; Hongjun Ren

doi:10.1055/s-0036-1591487

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(02): 349-360
DOI: 10.1055/s-0036-1591487

paper

Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones

Maozhong Miao *

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Huaping Xu

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Yi Luo

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Mengchao Jin

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Zhengkai Chen

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Jianfeng Xu

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

,

Hongjun Ren*

Department of Chemistry, Zhejiang Sci-Tech University (Xiasha Campus), Hangzhou, Zhejiang 310018, P. R. of China eMail: mmzok@zstu.edu.cn eMail: renhj@zstu.edu.cn

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Abstract

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Abstract

The catalyst-free Nazarov cyclization of aryl allenyl ketones under thermal condition is developed. Various densely functionalized 2,3-dihydroindanones or indenones are readily produced in moderate to excellent yields. Significantly, this procedure features high functional group tolerance and exclusive regioselectivity. The resulting substituted 2,3-dihydroindanones can be conveniently converted into valuable conjugated benzofulvene building blocks.

Key words

catalyst-free - Nazarov cyclization - indanones - benzofulvenes - allenes

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