97469-74-4

Upstream product

• 98-88-4 benzoyl chloride 
• 98-91-9 thiobenzoic acid 
• 64-04-0 phenethylamine 
• 65-85-0 benzoic acid 
• 611-73-4 Benzoylformic acid 
• 150-60-7 dibenzyl disulphide 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 100-52-7 benzaldehyde 
• 2227-79-4 benzenecarbothioamide 
• 103-82-2 phenylacetic acid 
• 108-88-3 toluene 
• 103-49-1 dibenzylamine 
• 100-46-9 benzylamine 
• 103-67-3 benzyl-methyl-amine 

Downstream Products

• 64-04-0 phenethylamine 
• 100-53-8 phenylmethanethiol 
• 130161-15-8 4-bromo-2,5-diphenylthiazole 

Relevant academic research and scientific papers

Ynamide-Mediated Thioamide and Primary Thioamide Syntheses

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.

Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur

A mild and chemoselective method for the thioacylation of amines using α-keto acids and elemental sulfur has been developed. The key to the success of this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol

Sulfur-Catalyzed Oxidative Coupling of Dibenzyl Disulfides with Amines: Access to Thioamides and Aza Heterocycles

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.).

Microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines: A rapid and efficient protocol for thioamides

An efficient protocol for synthesis of thioamides was developed via the microwave-Assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines. This process is scalable and tolerates a wide spectrum of amines to deliver the corresponding products in moderate to excellent yields in 10 minutes, providing a cheap and rapid approach to thioamides.

Oxidative Coupling-Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides

An efficient and selective multicomponent oxidative coupling, involving the use of two different amines, sodium phosphate, and elemental sulfur have been described for the preparation of thioamides, employing microwave irradiation. The use of an iron(III)-based imidazolium salt is essential as catalyst. Indeed, the iron-based catalyst is involved in the oxidative coupling of the two amines and in the subsequent C-S bond formation. The protocol is useful for a wide variety of primary benzylamines and alkylamines, as coupling partners. Thus, various electron-rich and electron-poor substituents in the aromatic rings and also fused piperidine derivatives, are suitable starting materials in this reaction. Some of the obtained products are important synthetic intermediates for natural products.

Preparation method of acetylene amide mediated thioacid amide and application of acetylene amide mediated thioacid amide in thiopeptide synthesis

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.

Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis

An efficient aqueous synthesis of thioamides through aldehydes, sodium sulfide, and N-substituted formamides has been developed. Both alkyl and aryl aldehydes are amenable to this protocol. N-Substituted formamides are essential for this transformation. Readily available inorganic salt (sodium sulfide) serves as the sulfur source in water, which makes this method much more practical and efficient. Furthermore, the late-stage modification of bioactive molecules and derivatives through this protocol has been established.

Iodine-Promoted Synthesis of Thioamides from 1,2-Dibenzylsulfane and Difurfuryl Disulfide

Thioamides can be generated at 100 °C in high yield through the reaction of 1,2-dibenzyldisulfane with difurfuryldisulfide using iodine as oxidant and DMSO as solvent. The protocol is metal- and additive-free, providing a convenient and economical way for the synthesis of various kinds of thioamides under mild conditions.

Selective thioacylation of amines in water: A convenient preparation of secondary thioamides and thiazolines

Primary thioamides have been utilised directly in water, without any derivatisation, to selectively thioacylate primary amines. By employing 2-hydroxyethylamines, the reaction can be extended to the preparation of 2-thiazolines via formation of β-hydroxythioamides.

H-β-zeolite catalyzed transamidation of carboxamides, phthalimide, formamides and thioamides with amines under neat conditions

Efficient transamidation of unactivated carboxamides, phthalimides, formamides and thioamides with amines under solvent-free conditions using H-β-zeolite as a green and recyclable heterogeneous catalyst is described. Easy work up, high purity of the products, recyclability and environmentally-friendly nature of the catalyst are the attractive features of the present methodology. This is the first report for the transamidation of thioamides under heterogeneous conditions.