Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes

Yi-Feng Qiu; Yue-Jie Niu; Xian-Rong Song; Xi Wei; Hui Chen; Shun-Xi Li; Xi-Cun Wang; Congde Huo; Zheng-Jun Quan; Yong-Min Liang

doi:10.1039/C9CC08286G

Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes†

Yi-Feng Qiu,

‡^a Yue-Jie Niu,‡^a Xian-Rong Song,

^b Xi Wei,^a Hui Chen,^a Shun-Xi Li,^a Xi-Cun Wang,

^a Congde Huo,*^a Zheng-Jun Quan

*^a and Yong-Min Liang

^c

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, People's Republic of China
E-mail: huocongde@nwnu.edu.cn, quanzhengjun@hotmail.com

^b Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science Technology Normal University, Nanchang, People's Republic of China

^c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, People's Republic of China
E-mail: liangym@lzu.edu.cn

Abstract

An iodine promoted cascade cycloisomerization of 1-en-6,11-diynes is presented for the easy preparation of tetrahydrobenzo[f]isoquinolines. This developed reaction system is identified as having good functional-group applicability and can be scaled up to gram quantities. In this transformation, two new cyclic frameworks and one carbonyl group are formed with four new bonds constructed. Additionally, the resulting iodo-substituted compounds could be further derived through simple elimination reactions.

Chemical Communications

Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes†

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Iodine promoted cascade cycloisomerization of 1-en-6,11-diynes

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