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Efficient Methods for the Synthesis of Novel Arylazothiazoles Based on Acetylferrocene or Adamantane.
Current Organic Synthesis ( IF 1.7 ) Pub Date : 2020-05-31 , DOI: 10.2174/1570179417666200226091711
Abdelwahed R Sayed 1 , Mohamed S M Ahmed 2 , Sobhi M Gomha 2
Affiliation  

Background: Hydrazonoyl halides are convenient for the synthesis of arylazothiazoles.

Materials and Methods: A series of novel arylazothiazoles were efficiently synthesized from the reaction of hydrazonoyl chlorides with 2-(adamantan-2-ylidene)hydrazinecarbothioamide or 2-(ferrocenyl-1-ylidene)hydrazinecarbo-- thioamide in dioxane used as an aprotic solvent because of its lower toxicity and higher boiling point (101 °C) and triethylamine at reflux. The reaction mechanistic pathway proceeded by the nucleophilic substitution reaction by the elimination of hydrogen chloride to give thiohydrazonates as intermediate, which in situ undergo intramolecular cyclization and loss of water molecule to afford the final product of novel arylazothiazoles. This method is simple with good yield and excellent purities.

Results and Discussion: The synthetic schemes for the final products are proposed and discussed. The chemical structures of the final products were identified by different techniques, such as elemental analysis, Fourier-transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS).

Conclusion: In this article, we prepared arylazothiazoles from the reaction of 2-(adamantan-2-ylidene)hydrazinecarbothioamide or 2-(ferrocenyl-1-ylidene)hydrazinecarbothioamide with hydrazonoyl halides.



中文翻译:

基于乙酰基二茂铁或金刚烷的新型芳基偶氮噻唑的合成方法。

背景:卤代酰卤便于合成芳基偶氮噻唑。

材料与方法:由酰氯与2-(金刚烷-2-亚甲基)肼基碳硫代酰胺或2-(二茂铁基-1-亚烷基)肼基碳-硫代酰胺在二恶烷中作为非质子溶剂反应,可有效合成一系列新型芳基偶氮噻唑。由于其毒性较低,沸点较高(101°C)和三乙胺回流。反应机理途径通过亲核取代反应进行,通过消除氯化氢得到硫代azo唑酸酯作为中间体,其原位经历分子内环化和水分子损失,从而得到新型芳基偶氮噻唑的最终产物。该方法简单,收率高,纯度高。

结果与讨论:提出并讨论了最终产品的合成方案。最终产品的化学结构是通过不同的技术鉴定的,例如元素分析,傅立叶变换红外光谱(FT-IR),核磁共振(NMR)和质谱(MS)。

结论:在本文中,我们是由2-(金刚烷-2-亚甲基)肼基碳硫代酰胺或2-(二茂铁基-1-亚烷基)肼基碳硫代酰胺与酰卤反应制备的芳基偶氮噻唑。

更新日期:2020-05-31
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