An efficient procedure for traceless solid-phase synthesis of N,N′-substituted thioureas by thermolytic cleavage of resin-bound dithiocarbamates

被引:34
作者
Gomez, L
Gellibert, F
Wagner, A
Mioskowski, C
机构
[1] Univ Louis Pasteur Strasbourg 1, Lab Synthese Bioorgan, CNRS UMR 7514, Fac Pharm, F-67401 Illkirch, France
[2] Lab Glaxo Wellcome, Ctr Rech, F-91951 Les Ulis, France
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2000年 / 2卷 / 01期
关键词
D O I
10.1021/cc990058d
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel and efficient procedure which is compatible with high-throughput process for the traceless solid-phase synthesis of thioureas is described. In the presence of carbon disulfide, Merrifield resin reacts with an amine to give a resin-bound dithiocarbamate moiety. Heating this supported dithiocarbamate in the presence of a second amine at 60 degrees C for 12 h led to the formation of the thiourea with the release of benzylthiol bound to the resin, This process allows the preparation of N,N'-di- and trisubstituted thioureas in good yields and with satisfactory purity. Furthermore, the mild reaction conditions involved are compatible with many functional groups.
引用
收藏
页码:75 / 79
页数:5
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