Categories: C-N Bond Formation >
Synthesis of thioamides
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Recent Literature
A microwave-enhanced Kindler thioamide synthesis is
introduced. The three-component condensations of aldehydes, amines, and
elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent
employing microwave flash heating at 110-180°C for 2-20 min. A simple workup
protocol allows the isolation of synthetically valuable thioamide building blocks in good yield and purity.
O. I. Zubruyev, N. Stiasni, C. O. Kappe, J. Comb. Chem., 2003, 5, 145-148.
O-Ethyl thioformate has been synthesized from triethylorthoformate and
hydrogen sulfide gas using sulfuric acid as Brønsted acid catalyst. The product
can be isolated as a neat liquid in 83% overall yield. Both the crude and
purified thiolate can be used to thioformylate various amines in good to
excellent yields.
C. J. Borths, J. Chan, B. J. Burke, R. D. Larsen, Synlett, 2009,
3139-3142.
Endothiopeptides can easily be obtained via Ugi reaction using thio acids as
acid components. If isonitriles with an acetal group are applied, the
endothiopeptides can directly be converted into thiazoles using TMSCl-NaI
under microwave irradiation.
U. Kazmaier, S. Ackermann, Org. Biomol. Chem., 2005, 3, 3184-3187.
