Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.
Molecules. 2013 Nov 28;18(12):14747-59. doi: 10.3390/molecules181214747.
OxymaPure (ethyl 2-cyano-2-(hydroxyimino)acetate) was tested as an additive for use in the carbodiimide (DIC) approach for the synthesis of a novel series of α-ketoamide derivatives (4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives). OxymaPure showed clear superiority to HOBt/DIC or carbodiimide alone in terms of purity and yield. The title compounds were synthesized via the ring opening of N-acylisatin. First, N-acetylisatin was reacted with 4-aminobenzoic acid under conventional heating as well as microwave irradiation to afford 4-(2-(2-acetamidophenyl)-2-oxoacetamido)benzoic acid. This α-ketoamide was coupled to different amino acid esters using OxymaPure/DIC as a coupling reagent to afford 4-[2-(2-acetylaminophenyl)-2-oxo-acetylamino]benzoyl amino acid ester derivatives in excellent yield and purity. The synthesized compounds were characterized using FT-IR, NMR, and elemental analysis.
OxymaPure（氰基乙酸乙酯）被测试为一种添加剂，用于合成一系列新型的α-酮酰胺衍生物（4-[2-（2-乙酰氨基苯基）-2-氧代乙酰氨基]苯甲酰氨基酸酯衍生物）的碳二亚胺（DIC）方法。与单独使用 HOBt/DIC 或碳二亚胺相比，OxymaPure 在纯度和产率方面具有明显优势。标题化合物通过 N-酰基靛红的开环合成。首先，N-乙酰靛红与 4-氨基苯甲酸在常规加热和微波辐射下反应，得到 4-（2-（2-乙酰氨基苯基）-2-氧代乙酰氨基）苯甲酸。该α-酮酰胺与不同的氨基酸酯在 OxymaPure/DIC 作为偶联试剂的条件下偶联，以优异的产率和纯度得到 4-[2-（2-乙酰氨基苯基）-2-氧代乙酰氨基]苯甲酰氨基酸酯衍生物。所合成的化合物通过傅里叶变换红外光谱（FT-IR）、核磁共振（NMR）和元素分析进行了表征。
