Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety

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. © 2017 Elsevier Ltd

Авторы
Tarasenko M.1 , Duderin N.2 , Sharonova T.2 , Baykov S.2 , Shetnev A. 3 , Smirnov A.V.2
Журнал
Издательство
Elsevier Ltd
Номер выпуска
37
Язык
Английский
Страницы
3672-3677
Статус
Опубликовано
Том
58
Год
2017
Организации
  • 1 Yaroslavl State Technical University, 88 Moscowsky Pr, Yaroslavl, 150023, 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
Ключевые слова
Anhydride; Carboxylic acid; Heterocycles; Room temperature synthesis; Superbase catalysis
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/5316/
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