Synthesis 2013; 45(6): 759-766
DOI: 10.1055/s-0032-1318139
paper
© Georg Thieme Verlag Stuttgart · New York

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

Zhenlan Yin
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Yu Wang
b   Key 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
b   Key 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
b   Key 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
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Zhihong Deng
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
,
Yiyuan Peng*
a   Key Laboratory of Green Chemistry, Jiangxi Province and College of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
b   Key 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
› Author Affiliations
Further Information

Publication History

Received: 18 December 2012

Accepted after revision: 08 January 2013

Publication Date:
05 February 2013 (online)


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.

Supporting Information