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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 5
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Original Articles

Traceless Approach for the Synthesis of 3,5-Disubstituted Thiohydantoins on Functionalized Ionic-Liquid Support

Chao Yao College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, China
,
Yandong Zhang College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, China
,
Guolin Zhang College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, China
,
Wenteng Chen College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, China
,
Yongping Yu College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, ChinaCorrespondence[email protected]
&
Richard A. Houghten College of Pharmaceutical Sciences, Zhejiang University, Zijin Campus, Hangzhou, China; Torry Pines Institute for Molecular Studies, San Diego, California, USA
Pages 717-724 | Received 24 May 2008, Published online: 04 Feb 2010
 
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Abstract

A traceless approach for the synthesis of 3,5-disubstituted thiohydantoins on a novel functionalized ionic-liquid support, 5, is described. Acylation of benzylamine functionalized ionic-liquid support with amino acids yielded ionic-liquid-supported amino acids, which reacted with isothiocyanates to afford ionic-liquid-supported thioureas. Following intramolecular cyclization cleavage from the ionic-liquid support by trifluoroacetic acid (TFA), the desired 3,5-disubstituted thiohydantoins were obtained in good yields and purities. The efficiency of this ionic-liquid-phase strategy facilitated isolation and analysis of intermediates and removal of excess reagents and by-products during the reaction process.

ACKNOWLEDGMENTS

Yongping Yu thanks the Foundation of NCET-05–0523, NSFC (No. 20572098), Zhejiang Science and Technology Program (No. 2005c34001), and 985 Platform of Zhejiang University. Richard A. Houghten thanks the National Science Foundation (No. CHE0455072).

Notes

a Isolated yield.

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