Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides

Abstract

Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies.

Synthesis, Spectral Characteristics, and Molecular Docking Studies of 2-(2,4-Dichlorophenoxy)-N-(2,2,2-trichloro-1-(3-arylthioureido)ethyl)acetamide

“…The starting materials for obtaining the target 2-( 2 3) was obtained through the condensation of chloral hydrate (1) with 2,4-dichlorophenoxyacetic acid amide (2) in the melt [24]. Next, the resulting compound 3 was chlorinated at the hydroxyl group, followed by the chlorine atom substitution in compound 4 for the isothiocyanate group according to the procedure described in [25]. Thioureas (7a-h) were obtained through the amines 6a-h addition to 2-(2,4-dichlorophenoxy)-N-(2,2,2-trichloro-1isothiocyanatoethyl)acetamide ( 5) in acetonitrile medium (Scheme 1).…”

“…White crystals; yield 90%; mp 123-125 (5). Isothiocyanate (5) was obtained through the stage of formation of the intermediate chlorine derivative (4) according to the procedure described in [25]. The product could not be isolated from the reaction mixture.…”

Synthesis, Spectral Characteristics, and Molecular Docking Studies of 2,4-Dichloro-N-(2,2,2-trichloro-1-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)amino)ethyl)benzamide

“…Synthesis of 2,4-dichloro-N-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)hydrazine-1-carbothioamido)ethyl)benzamide ( 3). An equimolar amount (1.67 g) of N-phenylhydra zinecarbothioamide (2) [54] was added to 10 mmol (3.78 g) of 2,4-dichloro-N-(2,2,2-trichloro-1-isothiocyanatoethyl)benzamide (1) [55,56] in 35 mL of acetonitrile. The mixture was refluxed for 1-3 min and then left for 24 h. The precipitate formed was filtered, washed with acetonitrile (2 × 10 mL), and dried.…”