97469-74-4Relevant 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.
Sulfur-Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles
Nguyen, Thanh Binh,Nguyen, Le Phuong Anh,Nguyen, Thi Thu Tram
supporting information, p. 1787 - 1791 (2019/02/26)
In the presence of catalytic amounts of elemental sulfur, dibenzyl disulfide/DMSO was found to be an excellent thiobenzoylating agent of amines to provide a wide range of thioamides. The reaction becomes autocatalytic when anilines substituted by an o-cyclizable group were used as nucleophile, leading to the corresponding 2-aryl aza heterocycles. (Figure presented.).
Preparation method of acetylene amide mediated thioacid amide and application of acetylene amide mediated thioacid amide in thiopeptide synthesis
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Paragraph 0047, (2018/09/21)
The invention discloses an acetylene amide mediated method for selectively synthesizing carbonyl thioesters and ordinary thioesters. The ordinary thioesters are further used for preparing amides and peptides, and the carbonyl thioesters are used for preparing thioamides and thiopeptides. An addition reaction is carried out between acetylene amide in m-xylene and thiocarboxylic acid to selectivelyobtain the carbonyl thioester and ordinary thioester of which the ratio is 3:1 under the condition of 40 DEG C below zero; the ordinary thioesters can carry out a combination reaction with amines to produce amides and peptides; and the carbonyl can carry out a combination reaction with the amines to produce thioamides and thiopeptides. The method disclosed by the invention is mild in reaction conditions, free of any metal catalyst, high in reaction speed, high in yield, simple in operation and wide in application range. With respect to chiral thiocarboxylic acid in a position alpha of carboxyl, when thioamide bonds or thiopeptide bonds are formed from the carbonyl thioesters or when amido bonds or peptide bonds are formed from the ordinary thioesters, any racemization phenomenon can be avoided.
