Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety |
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Authors: | Marina Tarasenko Nikolay Duderin Tatyana Sharonova Sergey Baykov Anton Shetnev Alexey V Smirnov |
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Institution: | 1. Yaroslavl State Technical University, 88 Moscowsky Pr, 150023 Yaroslavl, Russian Federation;2. Pharmaceutical Technology Transfer Center, Ushinsky Yaroslavl State Pedagogical University, 108 Respublikanskaya St., Yaroslavl 150000, Russian Federation;3. Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation |
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Abstract: | An efficient and mild one-pot protocol has been developed for the synthesis of 1,2,4-oxadiazoles via the reaction of amidoximes with dicarboxylic acid anhydrides in a NaOH/DMSO medium. The method allows the synthesis of diversely substituted carboxylic acids bearing the 1,2,4-oxadiazole motif, – a popular building block for pharmaceutical research, in moderate to excellent yields. The reaction scope includes aromatic and heteroaromatic amidoximes as well as five-, six- and seven-membered anhydrides. The advantages of this procedure are proven gram-scalability and the use of inexpensive starting materials, which from a process chemistry point of view are essential for future industrial applications. |
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Keywords: | Heterocycles Anhydride Carboxylic acid Superbase catalysis Room temperature synthesis |
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