Thioamides: Overview

Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides

“…The success in efficient hydrogenation of thioesters and the tolerance toward the generated thiol motivated us to study other organosulfur compounds, which are also widely used and ubiquitous in natural products and pharmaceuticals. 4 , 18 First, thiocarbamates were studied. To our surprise, all of the screened substrates were efficiently hydrogenated to the corresponding formamides and thiols, whereas in the case of the oxygen-based analogs, it is much harder to hydrogenate carbamates than amides and esters ( Scheme 6 , entries 1–3).…”

Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles

“…Thioamides, the closest O to S isosteres of amides in the strictest sense, have served as highly valuable motifs to accomplish synthetic processes. 12 With respect to the structural and electronic characteristics, thioamides feature a shorter C S bond than the analogous C O bond in amides. The weaker electronegativity of sulfur and the higher conjugation provide the higher contribution of the polar resonance form.…”

Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer

“…Dithiocarboxylic acids [1] or dithioesters [2] are common precursors of thioamides [3], a functional group that has found increasing uses over the last decade. In peptide chemistry, the thioamide function is a promising isostere of the amide group leading to interesting biological activities [4][5][6].…”