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Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2021-09-06 , DOI: 10.1134/s107042802107006x
S. O. Vardanyan 1 , A. S. Avagyan 1 , A. A. Aghekyan 1 , A. B. Sargsyan 1 , H. A. Panosyan 1
Affiliation  

Abstract

The addition of 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol to the C=C double bond of acrylonitrile, acrylamide, and ethyl acrylate afforded 3-[3-(1,4-benzodioxan-2-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoic acid nitrile, amide, and ethyl ester. The latter was converted to the corresponding hydrazide which reacted with substituted benzoyl chlorides to give unsymmetrical diacylhydrazines, and their cyclization by the action of phosphoryl chloride in toluene afforded tricyclic products containing 1,4-benzodioxane, 1,2,4-triazole, and 1,3,4-oxadiazole heterocycles.



中文翻译:

3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones 的 N-取代衍生物的合成

摘要

将 5-(1,4-benzodioxan-2-yl)-4-phenyl-4 H -1,2,4-triazole-3-thiol 添加到丙烯腈、丙烯酰胺和丙烯酸乙酯的 C=C 双键上得到 3-[3-(1,4-benzodioxan-2-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1 H -1,2,4-triazol-1-yl]propanoic acid 腈、酰胺和乙酯。后者转化为相应的酰肼,与取代的苯甲酰氯反应得到不对称的二酰基肼,它们在磷酰氯在甲苯中的作用下环化得到含有 1,4-苯二恶烷、1,2,4-三唑和 1 ,3,4-恶二唑杂环。

更新日期:2021-09-07
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