Synthesis 2018; 50(02): 349-360
DOI: 10.1055/s-0036-1591487
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones

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
,
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
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (21302169), the Natural Science Foundation of Zhejiang Province (LQ16B020001), the Science Foundation of Zhejiang Sci-Tech University (13062121-Y), and the Program for Innovative Research Team of Zhejiang Sci-Tech University (13060052-Y) for financial support.
Further Information

Publication History

Received: 03 August 2017

Accepted after revision: 13 September 2017

Publication Date:
09 October 2017 (online)

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.

Supporting Information

 
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