Synthesis of 4-Sulfanylcoumarins Using Thiourea and Alkyl Halides as the Sulfanylation Agent in Polyethylene Glycol–Water

Zhenlan Yin; Yu Wang; Qin Yang; Ying Wang; Jingshi Xu; Zhihong Deng; Yiyuan Peng

doi:10.1055/s-0032-1318139

Synthesis, Table of Contents

Synthesis 2013; 45(6): 759-766
DOI: 10.1055/s-0032-1318139

paper

Synthesis of 4-Sulfanylcoumarins Using Thiourea and Alkyl Halides as the Sulfanylation Agent in Polyethylene Glycol–Water

Zhenlan Yin

^aKey Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Yu Wang

^bKey Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120396 Email: yypeng@jxnu.edu.cn Email: yiyuanpeng@yahoo.com

,

Qin Yang

^bKey Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120396 Email: yypeng@jxnu.edu.cn Email: yiyuanpeng@yahoo.com

,

Ying Wang

^bKey Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120396 Email: yypeng@jxnu.edu.cn Email: yiyuanpeng@yahoo.com

,

Jingshi Xu

^aKey Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Zhihong Deng

^aKey Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

,

Yiyuan Peng*

^aKey Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China

^bKey Laboratory of Small Functional Organic Molecule, Ministry of Education and College of Life Science, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Fax: +86(791)88120396 Email: yypeng@jxnu.edu.cn Email: yiyuanpeng@yahoo.com

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Abstract

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Abstract

A novel and efficient route for the synthesis of 4-sulfanylcoumarins is disclosed. The direct sulfanylation of 4-tosyloxycoumarins with thiourea and various alkyl halides in polyethylene glycol 200–water (PEG 200–H₂O), at room temperature under an air atmosphere, affords the corresponding 4-sulfanylcoumarins in moderate to excellent yields. This transformation shows good substrate scope and takes place in a green solvent.

Key words

4-sulfanylcoumarins - 4-tosyloxycoumarins - thiourea - alkyl halides - polyethylene glycol 200

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References

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