Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates

Tao Wang; Rou Li; Danhong Yu; Chenghao Gu; Fei Xiong; Zhiyuan Chen

doi:10.1055/s-0034-1378654

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(23): 3213-3220
DOI: 10.1055/s-0034-1378654

paper

Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates

Tao Wang*

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

,

Rou Li

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

,

Danhong Yu

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

,

Chenghao Gu

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

,

Fei Xiong*

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

,

Zhiyuan Chen*

National Research Center for Carbohydrate Synthesis and Key Laboratory of Chemical Biology, Jiangxi Province, Jiangxi Normal University, 99 Ziyang Road, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120385 eMail: wangtao@jxnu.edu.cn eMail: xiongfei@jxnu.edu.cn eMail: zchen@jxnu.edu.cn

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Abstract

An efficient reaction of 2-alkynylbenzaldoximes with 2-isocyanoacetates cocatalyzed by silver triflate and gold(I) chloride is described, providing 1-aminoisoquinolines in good to excellent yields under mild conditions. Mechanistic experiments suggest that the gold(I) cation might play a crucial role in the activation of the isocyanide substrate. The observed reactivity and the unique pathway of substrate activation in the cocatalyzed processes are quite informative for further study.

Key words

1-aminoisoquinolines - coinage metals - deformylation - 2-alkynylbenzaldoximes - isocyanoacetates

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Referenzen

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