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J Comb Chem. 2000 Jan-Feb;2(1):75-9.

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

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  • 1Laboratoire de Synthèse Bioorganique, Université Louis Pasteur de Strasbourg, Unité associée au CNRS, UMR 7514 Faculté de Pharmacie, Illkirch, France.

Abstract

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.

PMID:
10750487
[PubMed - indexed for MEDLINE]
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