Regioselective Synthesis of Phenoxathiin Derivatives under Transition-Metal-Free Conditions

Fangdong Hu; Xin Zhao; Yanqiu Li; Lei Feng; Chen Ma

doi:10.1055/s-0032-1316863

Synthesis, Table of Contents

Synthesis 2013; 45(7): 966-970
DOI: 10.1055/s-0032-1316863

paper

Regioselective Synthesis of Phenoxathiin Derivatives under Transition-Metal-Free Conditions

Fangdong Hu

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China Fax: +86(531)88564464 Email: chenma@sdu.edu.cn

,

Xin Zhao

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China Fax: +86(531)88564464 Email: chenma@sdu.edu.cn

^bDepartment of Forensic Science and Technology, Shandong Police College, Jinan 250014, P. R. of China

,

Yanqiu Li

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China Fax: +86(531)88564464 Email: chenma@sdu.edu.cn

,

Lei Feng*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China Fax: +86(531)88564464 Email: chenma@sdu.edu.cn

,

Chen Ma*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China Fax: +86(531)88564464 Email: chenma@sdu.edu.cn

^cState Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China

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Abstract

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Abstract

A simple and efficient method was developed for the synthesis of phenoxathiin derivatives. A range of 1,2-dihaloarenes or 1-halo-2-nitroarenes reacted with 2-sulfanylphenol to give the desired products in good-to-excellent yields. It is intriguing that 1-halo-2-nitroarenes containing electron-donating groups worked well as substrates in this reaction.

Key words

regioselectivity - heterocycles - polycycles - cyclizations - fused-ring systems

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References

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