Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4‐Oxadiazole/Norborna(e)ne Hybrids

Baykov, Sergey V.; Tarasenko, M. V.; Зеленков, Лев Е.; Kasatkina, Svetlana O.; Savko, Polina Yu.; Shetnev, Аnton

doi:10.1002/ejoc.201900843

Cited by 13 publications

(6 citation statements)

References 60 publications

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“…As mentioned above, the cyclocondensation of O -acylamidoximes is a not so attractive method, and one-pot protocols, which start from amidoximes, are much more desirable, primarily, for drug discovery. The possibility of carrying out the reaction in a “two-step, one-pot” manner is the main advantage of the MOH/DMSO system (M = Li, Na, K) in comparison with TBAF-involved methods, and it was realized in several works [ 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 ]. It is most convenient to discuss these methods by dividing them by the type of used carboxyl function sources: esters, acids, acyl chlorides, anhydrides, dicarboxylic acid anhydrides, aldehydes, and even N -acyl benzotriazoles.…”

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

“…The synthesis of 1,2,4-oxadiazole bearing carboxylic functionality via the one-pot condensation of amidoximes and dicarboxylic acid anhydrides is one of the major benefits from the exploitation of the MOH/DMSO medium [ 98 , 99 , 100 , 101 , 102 ]. Notably, successful examples of the base-catalyzed condensation of O -acylamidoximes containing carboxylic functionality are not described.…”

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

“…Moreover, previously undescribed 1,2,4-oxadiazole/norborna(e)ne hybrids were synthesized from norbornene and norbornane dicarboxylic acids anhydrides according to this procedure ( Scheme 21 ) [ 99 ]. The feature of this reaction is an epimerization and the mentioned 1,2,4-oxadiazole/norborna(e)ne hybrids were obtained as trans -diastereomers, whereas the starting anhydrides had cis -conformation.…”

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

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Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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1,2,4-Oxadiazole is an essential motif in drug discovery represented in many experimental, investigational, and marketed drugs. This review covers synthetic methods that allow the conversion of different types of organic compounds into 1,2,4-oxadiazole at ambient temperature and the practical application of the latter approaches for the preparation of pharmaceutically important molecules. The discussed methods are divided into three groups. The first combines two-stage protocols requiring the preliminary preparation of O-acylamidoximes followed by cyclization under the action of organic bases. The advantages of this route are its swiftness, high efficiency of the cyclization process, and uncomplicated work--up. However, it requires the preparation and isolation of O-acylamidoximes as a separate preliminary step. The second route is a one-pot synthesis of 1,2,4-oxadiazoles directly from amidoximes and various carboxyl derivatives or aldehydes in aprotic bipolar solvents (primarily DMSO) in the presence of inorganic bases. This recently proposed pathway proved to be highly efficient in the field of medicinal chemistry. The third group of methods consists of diverse oxidative cyclizations, and these reactions have found modest application in drug design thus far. It is noteworthy that the reviewed methods allow for obtaining 1,2,4-oxadiazoles with thermosensitive functions and expand the prospects of using the oxadiazole core as an amide- or ester-like linker in the design of bioactive compounds.

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Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

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Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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“…We have come close to solving this problem by developing methodology to synthesis of 1,2,4-oxadizoles form amidoximes and carboxylic acid derivatives in MOH/DMSO medium at ambient temperature. [34][35][36][37] This approach allows to obtain 1,2,4oxadiazoles with diverse functionalities, including C=C multiple bonds, [38] urea [39,40] and carboxylic substituents, [41][42][43] as well as animo-groups. [44][45][46] It was found that some anilines bearing 1,2,4-oxadiazole moiety intensely emit in the blue region.…”

Section: Introductionmentioning

confidence: 99%

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

et al. 2022

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Condensation of amidoximes 1 with isatoic anhydrides 2 or esters 3 in NaOH/DMSO medium afforded to substituted 1,2,4oxadiazolyl anilines. The compounds synthesized can exhibit luminescence, the presence and efficiency of which depends on the position of the amino group in these aminophenyl 1,2,4-oxadiazol derivatives. The best luminophores are 2-(ortho-aminophenyl) 1,2,4-oxadiazoles. More than 20 examples of the new organic luminophores were synthesized and studied. The effect of the luminophore structure on the emission band and on the quantum yield indicates that a luminescent scaffold has been obtained.

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“…The type of the formed heterocyclic core depends mainly on the structure of the electrophile. In particular, the coupling of amidoximes with carbonyl-based compounds such as aldehydes [ 7 , 8 , 9 ], carboxylic acids [ 10 , 11 , 12 ], and their derivatives (esters [ 13 , 14 , 15 , 16 ], anhydrides [ 17 , 18 , 19 , 20 ], as well as acyl chlorides [ 21 , 22 , 23 , 24 ]) usually results in 1,2,4-oxadiazoles. In this case, both nucleophilic centers of amidoxime (NOH and NH 2 groups) attack the same carbon atom of the electrophile ( Scheme 1 A).…”

Section: Introductionmentioning

confidence: 99%

Unusual Formation of 1,2,4-Oxadiazine Core in Reaction of Amidoximes with Maleic or Fumaric Esters

et al. 2022

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We have developed a simple and convenient method for the synthesis of 3-aryl- and 3-hetaryl-1,2,4-oxadiazin-5-ones bearing an easily functionalizable (methoxycarbonyl)methyl group at position 6 via the reaction of aryl or hetaryl amidoximes with maleates or fumarates. The conditions for this reaction were optimized. Different products can be synthesized selectively in good yields depending on the base used and the ratio of reactants: substituted (1,2,4-oxadiazin-6-yl)acetic acids, corresponding methyl esters, or hybrid 3-(aryl)-6-((3-(aryl)-1,2,4-oxadiazol-5-yl)methyl)-4H-1,2,4-oxadiazin-5(6H)-ones. The reaction is tolerant to substituents’ electronic and steric effects in amidoximes. As a result, a series of 2-(5-oxo-3-(p-tolyl)-5,6-dihydro-4H-1,2,4-oxadiazin-6-yl)acetic acids, their methyl esters, and 1,2,4-oxadiazoles based on them were prepared and characterized by HRMS, 1H, and 13C NMR spectroscopy. The structures of three of them were elucidated with X-ray diffraction.

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Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4‐Oxadiazole/Norborna(e)ne Hybrids

Cited by 13 publications

References 60 publications

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

2‐(1,2,4‐Oxadiazol‐5‐yl)aniline as a New Scaffold for Blue Luminescent Materials

Unusual Formation of 1,2,4-Oxadiazine Core in Reaction of Amidoximes with Maleic or Fumaric Esters

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