35960-95-3Relevant articles and documents
Ynamide-Mediated Thioamide and Primary Thioamide Syntheses
Wang, Changliu,Han, Chunyu,Yang, Jinhua,Zhang, Zhenjia,Zhao, Yongli,Zhao, Junfeng
, p. 5617 - 5629 (2022/04/22)
Environmentally friendly ynamide-mediated thioamidation of monothiocarboxylic acids with amines or ammonium hydroxide for the syntheses of thioamides and primary thioamides is described. Simple and mild reaction conditions enable the reaction to tolerate a wide variety of functional groups such as hydroxyl group, ester, tertiary amine, ketone, and amide moieties. Readily available NaSH served as the sulfur source, avoiding the use of toxic, expensive, and malodorous organic sulfur reagents and making this strategy environmentally friendly and practical. Importantly, the stereochemical integrity of α-chiral monothiocarboxylic acids was maintained during the activation step and subsequent aminolysis process, thus offering a racemization-free strategy for peptide C-terminal modification. Furthermore, a number of thioamide-modified drugs were prepared in good yields by using this protocol and the synthesized primary thioamides were transformed into backbone thiazolyl modified peptides.
Reactions of thioesters with organic azides - A novel access to imidates and thioimidates
Mloston,Romanski,Heimgartner
, p. 975 - 982 (2007/10/03)
The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the "twofold extrusion" of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.
