Synthesis and spectral characteristics of N-(2,2,2-trichloro-1-((5-(R-amino)-1,3,4-thiadiazol-2-yl)amino)ethyl)carboxamides

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2024-12-01 DOI:10.1080/00397911.2024.2422472

Valeriia V. Pavlova , Pavlo V. Zadorozhnii , Aleksey B. Ryabitsky , Vadym V. Kiselev , Oxana V. Okhtina , Aleksandr V. Kharchenko

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引用次数: 0

Abstract

In this paper, we reported the development of an efficient and highly productive synthetic protocol for preparing new 2,5-diamino-1,3,4-thiadiazole derivatives functionalized with N-(2,2,2-trichloroethyl)carboxamide group. The method of their preparation was based on the reaction of oxidative dehydrosulfurization of N-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)hydrazine-1-carbothioamido)ethyl)carboxamides and N-(1-(2-carbamothioylhydrazine-1-carbothioamido)-2,2,2-trichloroethyl)benzamide under the action of a mixture of iodine and triethylamine in DMF. This reaction took place at room temperature for two hours and allowed obtaining the target products with a 69-75% yield. Using the developed protocol, we obtained ten new derivatives of 1,3,4-thiadiazole. Their structure was proven by IR,¹H NMR,¹³C NMR, ¹H-¹H COSY, ¹H-¹³C HSQC, ¹H-¹³C HMBC spectroscopy, and LC/HRMS spectrometry.

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N-（2,2,2-三氯-1-（（5-（r -氨基）-1,3,4-噻二唑-2-基）氨基）乙基）羧酰胺的合成及光谱特性

本文报道了以N-（2,2,2-三氯乙基）羧基为官能团的新型2,5-二氨基-1,3,4-噻二唑衍生物的高效合成方法。它们的制备方法是在DMF中碘和三乙胺的混合物作用下，N-（2,2,2-三氯-1-（2-（苯基氨基甲氧基）肼-1-碳硫氨基）乙基）甲酰胺和N-（1-（2-氨基氨基甲氧基）肼-1-碳硫氨基）-2,2,2-三氯乙基)苯酰胺的氧化脱氢硫化反应。该反应在室温下进行了2小时，并允许以69-75%的产率获得目标产物。利用该方法，我们得到了10个新的1,3,4-噻二唑衍生物。通过IR、1H NMR、13C NMR、1H COSY、1H-13C HSQC、1H-13C HMBC、LC/HRMS等方法证实了它们的结构。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.