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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.