Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence

Sofia Presnukhina, Marina Tarasenko, Sergey Baykov, Sergey N. Smirnov, Vadim P. Boyarskiy, Anton Shetnev, Mikhail K. Korsakov

Результат исследований: Научные публикации в периодических изданияхстатья

Аннотация

A simple and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed retro-Diels-Alder reaction. The observed stereoselective heterocyclization/retro-Diels-Alder cascade process is suitable for the synthesis of a wide range of substituted (E)-1,2,4-oxadiazole-5-ylacrylic acids featuring electron donating and electron withdrawing groups on the aryl moiety, as well as heteroaryl or alkyl substituents at position 3 of the 1,2,4-oxadiazole ring (42–79%; 15 examples).

Язык оригиналаанглийский
Номер статьи151543
Число страниц4
ЖурналTetrahedron Letters
Том61
Номер выпуска9
Ранняя дата в режиме онлайн19 ноя 2019
DOI
СостояниеОпубликовано - 27 фев 2020

Предметные области Scopus

  • Органическая химия
  • Поиск новых лекарств
  • Биохимия

Fingerprint Подробные сведения о темах исследования «Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence». Вместе они формируют уникальный семантический отпечаток (fingerprint).

  • Цитировать