Synthesis 2013; 45(7): 966-970
DOI: 10.1055/s-0032-1316863
paper
© Georg Thieme Verlag Stuttgart · New York

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

Fangdong Hu
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Fax: +86(531)88564464   eMail: chenma@sdu.edu.cn
,
Xin Zhao
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Fax: +86(531)88564464   eMail: chenma@sdu.edu.cn
b   Department of Forensic Science and Technology, Shandong Police College, Jinan 250014, P. R. of China
,
Yanqiu Li
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Fax: +86(531)88564464   eMail: chenma@sdu.edu.cn
,
Lei Feng*
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Fax: +86(531)88564464   eMail: chenma@sdu.edu.cn
,
Chen Ma*
a   School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. of China   Fax: +86(531)88564464   eMail: chenma@sdu.edu.cn
c   State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China
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Publikationsverlauf

Received: 30. Dezember 2012

Accepted after revision: 06. Februar 2013

Publikationsdatum:
28. Februar 2013 (online)


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.

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