61349-98-2

Upstream product

• 120-75-2 2-Methylbenzothiazole 
• 62-53-3 aniline 
• 95-16-9 1,3-Benzothiazole 
• 103-72-0 phenyl isothiocyanate 
• 98-95-3 nitrobenzene 
• 6890-75-1 Phenylaminothioxoacetic Acid 
• 1457-85-8 Ethyl oxanilate 
• 37859-43-1 2-chloromethylbenzothiazole 
• 92081-75-9 benzothiazole-2-dithiocarboxylate methyl ester 
• 6244-74-2 N,N'-diphenyldithiooxamide 
• 56934-77-1 2-thioxo-2-phenylaminoacetic acid ethyl ester 
• 78121-70-7 N,N'-diphenylthiooxamide 

Downstream Products

• 109382-93-6 2-(5-Chloromethyl-4-phenyl-4H-[1,2,4]triazol-3-yl)-benzothiazole 
• 115924-89-5 C₁₄H₁₂N₄S 

Relevant academic research and scientific papers

Functionalization of primary ch bonds in picolines toward pyridylthioamides

We report a method for coupling of nitroarenes, 2- or 4-methylazaarenes, and elemental sulfur to afford (2-pyridyl)aryl thioamides. Good tolerance of functionalities was observed, including primary and secondary amines, bromo, iodo, ester, and boronic est

Synthesis of benzofuran, benzothiophene, and benzothiazole-based thioamides and their evaluation as KATP channel openers

Several series of benzofurans, benzothiophenes, and benzothiazoles, all featuring the thioamide group, were synthesized and tested as novel K ATP channel openers in artificial cell systems: CHO cells transfected with SUR1/Kir6.2, and HEK 293 cells transfected with SUR2B/Kir6.1; these served as model systems for insulin-secreting pancreatic β cells and smooth muscle cells, respectively. All compounds were investigated with respect to their binding affinity for the SUR2B-type KATP channels using [ 3H]P1075 as radioligand. Selected compounds were also tested as agonists in intact cells using DiBAC4(3) and DyeB (R7260) as membrane potential dyes. Remarkable affinity for SUR2B/Kir6.1 channels in the single-digit micromolar range was observed. In addition, benzothiazole-derived thioamides with sterically demanding, lipophilic substituents showed >100-fold selectivity in favor of SUR2B/Kir6.1. A one-carbon spacer between the heterocyclic skeleton and the thioamide moiety was observed to be crucial for affinity and selectivity. Two of the most potent and selective compounds were studied by crystal structure analyses.

Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with Sulfur

With a mixture of sulfur and amine in DMF at room temperature halomethyl compounds (1,5-10) can be oxidized to give thiocarboxylic acids (2,11-16) and their derivatives (3,4,17-35).We studied this reaction in detail especially with chloroacetic derivatives (11-15) or chloromethyl heterocycles (16) formally derived from chloroacetic acid.The resulting thiooxalic acid derivatives (11-27) represent activated acids and very useful C2-synthons, especially for the synthesis of heterocycles.Oxidation in the presence of triethylamine leads to dithiocarboxylates (11-16) which can be alkylated to dithioesters (17-27) in high yields.As a rule, with different primary and secondary amines instead of tertiary amines these dithiocarboxylates or dithiocarboxylic esters can be transformed already at low temperatures to thioamides (28-35).

SYNTHESIS AND SPECTROMETRIC INVESTIGATION OF THE THIOAMIDES OF THIAZOLE- AND BENZOTHIAZOLE-2-CARBOXYLIC ACIDS

The reaction of 2-lithiumthiazole and benzothiazole with isothiocyanates gave the corresponding thioamides.Based on the IR, UV, and PMR spectra it was established that an intramolecular hydrogen bond is formed in these thioamides between the NH fragment o