Dualism of 1,2,4-oxadiazole ring in noncovalent interactions with carboxylic group

Baykov, Sergey V.; Tarasenko, M. V.; Semenov, Artem V.; Катленок, Е. А.; Shetnev, Аnton; Boyarskiy, Vadim P.

doi:10.1016/j.molstruc.2022.132974

Cited by 6 publications

(5 citation statements)

References 96 publications

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“…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. The same inversion was also observed for the reaction of amidoximes with anhydrides of cyclohexane- and cyclohexene-1,2-dicarboxylic acids [ 100 ]. Although the detailed mechanism of epimerization is not clear hitherto, strong basic conditions are of key importance.…”

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

confidence: 66%

“…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%

“…Although the detailed mechanism of epimerization is not clear hitherto, strong basic conditions are of key importance. For example, the same reaction in the presence of K 2 CO 3 in 1,4-dioxane provides cis -isomers ( Scheme 21 ) [ 99 , 100 ].…”

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...supporting

confidence: 66%

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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“…Independent gradient model based on Hirshfeld partition. IGMH is a useful technique to visually study the interactions between fragments, 58,59 and it is inspired by the IGM 55 method. IGM introduced a descriptor, dg, to reveal the regions and strength of intramolecular or intermolecular interactions.…”

Section: Computationalmentioning

confidence: 99%

Glycine in a basket: protonated complexes of 1,1,n,n-tetramethyl[n](2,11)teropyrenophane (n = 7, 8, 9) with glycine in the gas-phase

Chen

Ghasemabadi

Bodwell

et al. 2023

Phys. Chem. Chem. Phys.

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Aromatic‐Carbonyl Interactions as an Emerging Type of Non‐Covalent Interactions

Yin,

Ye,

Hai

et al. 2024

Advanced Science

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Aromatic‐carbonyl (Ar···C═O) interactions, attractive interactions between the arene plane and the carbon atom of carbonyl, are in the infancy as one type of new supramolecular bonding forces. Here the study and functionalization of aromatic‐carbonyl interactions in solution is reported. A combination of aromatic‐carbonyl interactions and dynamic covalent chemistry provided a versatile avenue. The stabilizing role and mechanism of arene‐aldehyde/imine interactions are elucidated through crystal structures, NMR studies, and computational evidence. The movement of imine exchange equilibria further allowed the quantification of the interplay between arene‐aldehyde/imine interactions and dynamic imine chemistry, with solvent effects offering another handle and matching the electrostatic feature of the interactions. Moreover, arene‐aldehyde/imine interactions enabled the reversal of kinetic and thermodynamic selectivity and sorting of dynamic covalent libraries. To show the functional utility diverse modulation of fluorescence signals is realized with arene‐aldehyde/imine interactions. The results should find applications in many aspects, including molecular recognition, assemblies, catalysis, and intelligent materials.

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Dualism of 1,2,4-oxadiazole ring in noncovalent interactions with carboxylic group

Cited by 6 publications

References 96 publications

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

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

Glycine in a basket: protonated complexes of 1,1,n,n-tetramethyl[n](2,11)teropyrenophane (n = 7, 8, 9) with glycine in the gas-phase

Aromatic‐Carbonyl Interactions as an Emerging Type of Non‐Covalent Interactions

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