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Synthesis of Novel N-(R)-2-(1-Adamantyl)-1H-Benzimidazole-5(6)- Carboxamide, Carbohydrazide and 1,3,4-Oxadiazole Derivatives
Letters in Organic Chemistry ( IF 0.7 ) Pub Date : 2021-05-31 , DOI: 10.2174/1570178617999200812134408
Marina Soselia 1 , Medea Lomidze 1 , Tamar Tabatadze 1 , Davit Zurabishvili 1 , Marina Trapaidze 1 , Shota Samsoniya 1
Affiliation  

A novel series of benzimidazole-5(6)-carboxamide 3a-g, carbohydrazide 5a-e and 1,3,4- oxadiazole 6a-g derivatives bearing adamantane moiety were synthesized. The synthesis of benzimidazole heterocycle was performed by direct condensation/cyclization reaction of 1- adamantanecarboxylic acid with methyl 3,4-diaminobenzoate in Trimethylsilyl Polyphosphate (PPSE). The obtained Methyl 2-(1-adamantyl)-1H-benzimidazole-5(6)-carboxylate was converted to desired carboxamide and carbohydrazide derivatives in two different ways. In the first case, the synthesized ester after hydrolysis was converted to an acid chloride and subsequently coupled with different aromatic and heterocycle amines to give carboxamide derivatives. In the second case, treatment with hydrazine hydrate gave corresponding 2-(1-adamantyl)-1H-benzimidazole-5(6)-carbohydrazide which was coupled with some acyl chlorides to give appropriate carbohydrazide derivatives and with some aromatic acids to give 1,3,4-oxadiazole derivatives.



中文翻译:

新型 N-(R)-2-(1-Adamantyl)-1H-Benzimidazole-5(6)- Carboxamide、Carbohydrazide 和 1,3,4-Oxadiazole 衍生物的合成

合成了一系列带有金刚烷部分的苯并咪唑-5(6)-甲酰胺 3a-g、碳酰肼 5a-e 和 1,3,4-恶二唑 6a-g 衍生物。苯并咪唑杂环的合成是通过 1-金刚烷羧酸与 3,4-二氨基苯甲酸甲酯在三甲基甲硅烷基聚磷酸酯 (PPSE) 中的直接缩合/环化反应进行的。以两种不同的方式将获得的 2-(1-金刚烷基)-1H-苯并咪唑-5(6)-羧酸甲酯转化为所需的甲酰胺和甲酰肼衍生物。在第一种情况下,水解后合成的酯转化为酰氯,随后与不同的芳香胺和杂环胺偶联,得到甲酰胺衍生物。在第二种情况下,

更新日期:2021-06-04
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