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Synthesis 2019; 51(11): 2397-2401
DOI: 10.1055/s-0037-1610862
paper
© Georg Thieme Verlag Stuttgart · New York

A Facile and Efficient Approach for the Synthesis of 3-Aryl-4-hydroxy-1,3-thiazolidin-2-ones

Yue Zhu
a   Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
,
Qilin Wang
b   School of Biological and Pharmaceutical Engineering, Wuhan Polytechnic University, Wuhan, Hubei 430000, P. R. of China
,
Haofan Luo
a   Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
,
Zijuan Wang
a   Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
,
Guolin Zhang*
a   Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
,
Yongping Yu*
a   Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Zhejiang 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
› Author AffiliationsThis project was supported by Natural Science Foundation of Zhejiang Province (Grant No. LY16H300001) to G. Zhang and National Natural Science Foundation of China (Grant No. 81673291 and 81473074) and Osteoporosis & Breast Cancer Research Center, U.S.A. to Y. Yu.
Further Information

Publication History

Received: 04 November 2018

Accepted after revision: 01 February 2019

Publication Date:
01 April 2019 (online)

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§ Yue Zhu and Qilin Wang contributed equally to this work.

Abstract

A facile and efficient method for the synthesis of 3-aryl-4-hydroxy-1,3-thiazolidin-2-ones by the reaction of 1,4-dithiane-2,5-diol with acyl azides is reported. This reaction proceeded well at 80 °C to afford products in excellent yields for a wide range of substrates. A possible mechanism has been proposed.

Key words

3-aryl-4-hydroxy-1,3-thiazolidin-2-ones - 1,4-dithiane-2,5-diol - acyl azide - nucleophilic addition - facile synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610862.
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