Novel Method for Producing Thiono Derivatives Useful in Drug Synthesis
Thionation, the conversion of a carbonyl group to the corresponding thiocarbonyl group, is a standard method for the preparation of a variety of useful organosulfur derivatives, including thionoesters, thionolactones, thioamides, etc. To date, the best reagent for bringing about this transformation has been Lawesson’s reagent (LR). However, LR has two drawbacks which limit its usefulness: it is expensive, and the large amount of reagent-derived byproducts which accompany its reactions can only be removed by chromatography. Both of these drawbacks tend to limit application of LR to small-scale preparations. A researcher at Dartmouth has developed a new reagent for thionations which circumvents the disadvantages of LR. The new reagent is cheap, reagent-derived byproducts may be removed by simple hydrolytic procedures, and yields are comparable to those obtained with LR. This new thionation reagent should be especially useful for the large-scale preparation of intermediates, such as those involved in drug synthesis and other processes in the chemical industry. Further, the difficulties in producing large quantities of thiono derivatives have hampered development of applications for these versatile intermediates. The new reagent developed at Dartmouth should stimulate interest in and demand for these compounds, presenting an opportunity for the suppliers of fine chemicals.
Dartmouth has filed a patent application claiming this technology. We are seeking an industrial partner who is interested in the commercialization of this technology. (Ref: J146)
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