- 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
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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).
- Presnukhina, Sofia,Tarasenko, Marina,Baykov, Sergey,Smirnov, Sergey N.,Boyarskiy, Vadim P.,Shetnev, Anton,Korsakov, Mikhail K.
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supporting information
(2019/12/27)
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- Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids
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A one-pot ambient-temperature procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from amidoximes and carboxylic acids under superbase-promoted conditions is reported.
- Sharonova, Tatyana,Pankrat'eva, Vitalina,Savko, Polyna,Baykov, Sergey,Shetnev, Anton
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supporting information
p. 2824 - 2827
(2018/06/13)
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- Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype
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We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biologi
- Krasavin, Mikhail,Sosnov, Andrey V.,Karapetian, Ruben,Konstantinov, Igor,Soldatkina, Olga,Godovykh, Elena,Zubkov, Fedor,Bai, Ruoli,Hamel, Ernest,Gakh, Andrei A.
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p. 4477 - 4481
(2015/02/19)
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- 6-Substituted pyridoindolone derivatives, production and therapeutic use thereof
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Compounds of formula: and pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R1, R2, R3, R4, and R5, have the meanings given in the description; pharmaceutical compositions comprising said compounds; and processes for preparing said compounds and methods of use thereof.
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Page/Page column 21
(2010/11/27)
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