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Relevant academic research and scientific papers

Aminonitrones as highly reactive bifunctional synthons. An expedient one-pot route to 5-amino-1,2,4-triazoles and 5-amino-1,2,4-oxadiazoles-potential antimicrobials targeting multi-drug resistant bacteria

The developed one-pot protocol to 5-amino-1,2,4-triazoles or 5-amino-1,2,4-oxadiazoles includes an interplay between aminonitrones R1C(NH2)N+(Me)O- (R1 = Alk, Ar, Het), isocyanides R2NC (R2 = Alk, Ar), Br2, and hydrazines (for the triazoles) or hydroxylamine (for the oxadiazoles). This formally four-component reaction, involving aminonitrones, isocyanides, bromine, and N-nucleophiles, proceeds very rapidly under mild conditions (10 min, 20-25 °C), and is insensitive to moisture and air (in undried CHCl3-MeOH, in air) and it gives the heterocyclic systems in good yields (up to 86%; 26 examples). The reaction scope includes aromatic-, heteroaromatic-, and aliphatic aminonitrones and also aliphatic- and aromatic isocyanides. Results of DFT calculations (M06-2X/6-311+G(d,p) level of theory) indicate that the O-nucleophilic center of bifunctional aminonitrones is more reactive than the N center; it first reacts with in situ generated R2NCBr2 to grant 2-methyl-1,2,4-oxadiazolium salts, which are then converted to the target heterocyclic systems upon treatment with hydrazines or hydroxylamine. The nature and strength of the intramolecular hydrogen bonds N-H?N and O-H?N, which significantly contribute to the total energies of different transition states and products of the nucleophilic substitution, were studied theoretically using the topological analysis of the electron density distribution within the framework of Bader's theory (QTAIM method). Several new 5-amino-3-aryl-1,2,4-triazoles and -1,2,4-oxadiazoles exhibit high antibacterial activity against multidrug-resistant bacteria strains such as Staphylococcus aureus and Klebsiella pneumoniae (MIC = 8 mg L-1).

Synthesis of alkynylated 1,2,4-oxadiazole/1,2,3-1H-triazole glycoconjugates: Discovering new compounds for use in chemotherapy against lung carcinoma and Mycobacterium tuberculosis

A total of forty-three compounds were synthesized, including thirty-two new ones. Among those compounds, seventeen were selected and tested on human tumor cell lines: PC-3 (prostate adenocarcinoma), HCT-116 (colorectal tumor), NCIH-460 (lung carcinoma), S

Palladium-catalyzed synthesis of 5-amino-1,2,4-oxadiazoles via isocyanide insertion

A convenient and efficient palladium-catalyzed approach has been developed for the synthesis of 5-amino-1,2,4-oxadiazoles from amidoximes and isocyanides. Various 5-amino-1,2,4-oxadiazoles were obtained in moderate to high yields under mild conditions. The key to the success of this strategy involves new C-N bond and C-O bond formation via palladium-catalyzed isocyanide insertion.

Facile selective synthesis of 2-methyl-5-amino-1,2,4-oxadiazolium bromides as further targets for nucleophilic additions

The reaction of aminonitrones R1C(NH2) = N+(Me)O- (R1 = Alk, Ar) with isocyanides R2NC (R2 = Alk, Ar; 1.2 equiv.) and Br2 (1 equiv.) conducted in CHCl3 (RT, 5 min) gives 2-methyl-5-amino-1,2,4-oxadiazolium bromides in good to excellent yields (65-95%; 16 examples). These species are highly electrophilically activated and 5-cyclohexylamino-2-methyl-3-phenyl-1,2,4-oxadiazolium bromide, taken as a model compound for the reactivity study, reacts rapidly under mild conditions with hydroxylamine, hydrazine, or benzamidine, to give 5-cyclohexylamino-3-phenyl-1,2,4-oxadiazole (88%), 5-cyclohexylamino-3-phenyl-1,2,4-triazole (95%), and 2-cyclohexylamino-4,6-diphenyl-1,3,5-triazine (64%), respectively. Treatment of the oxadiazolium salt with excess water provides N-benzoyl-N′-cyclohexylurea (95%).

Focused microwave irradiation-assisted synthesis of N-cyclohexyl-1,2,4-oxadiazole derivatives with antitumor activity

A facile synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives under focused microwave irradiation (FMWI) is reported. Arylamidoximes 1a–i and dicyclohexylcarbodiimide (DCC) were carried out in DMF under FMWI to obtain 1,2,4-oxadiazoles 2a–i in 61–8

Multicomponent Reaction of Z-Chlorooximes, Isocyanides, and Hydroxylamines as Hypernucleophilic Traps. A One-Pot Route to Aminodioximes and Their Transformation into 5-Amino-1,2,4-oxadiazoles by Mitsunobu-Beckmann Rearrangement

Synthetically useful aminodioximes are prepared via a novel three-component reaction among Z-chlorooximes, isocyanides, and hydroxylamines by exploiting the preferential attack of isocyanides to nitrile N-oxides via a [3 + 1] cycloaddition reaction. The r

An efficient one-pot synthesis of 3-aryl-1,2,4-oxadiazol-5-amines under solvent-free conditions

The in situ prepared amidoximes from the reaction between nitriles and hydroxylamine are condensed with carbodiimides in the presence of molecular sieves under solvent-free conditions to produce the title compounds in excellent yields.

Convenient synthesis and biological profile of 5-amino-substituted 1,2,4-oxadiazole derivatives

We describe herein a convenient straightforward synthesis of 5-amino-substituted 1,2,4-oxadiazoles, upon the reactions of amidoximes with carbodiimides, as well as their further derivatization to acetamides, in good yields. Most of the compounds exhibited in general low interaction with the stable radical 1,1-diphenyl-2-picryl-hydrazyl. Compounds 32 and 39 inhibited significantly soybean lipoxygenase. Selected compounds were screened for their in vivo anti-inflammatory activity using the carrageenin paw edema model and showed significant anti-inflammatory activity (26, 51%). The ability of the compounds to release NO in the presence of a thiol factor has been also investigated.

A convenient synthesis of 5-amino-substituted 1,2,4-oxadiazole derivatives via reactions of amidoximes with carbodiimides

5-Amino substituted 1,2,4-oxadiazole derivatives were easily prepared, in one step and in high yields, via reactions of a variety of aryl, benzyl, cycloalkyl and alkyl amidoximes with commercially available carbodiimides. Alkyl carbodiimides reacted with amidoximes in toluene to give 5-alkylamino-l,2,4-oxadiazoles, whereas aromatic carbodiimide reacted in DMF to give initially the intermediate O-amidoxime adducts, which were further cyclized to the corresponding 5-arylamino-1,2,4-oxadiazoles.

An efficient one-pot synthesis of 5-(substituted amino)-1,2,4-thia- and -oxa-diazoles

A general protocol for the synthesis of 5-(substituted amino)-1,2,4- thiadiazoles by the cyclocondensation reaction of amidoximes with N-substituted thioureas in the presence of KF/Al2O3, and of 5-(cyclohexylamino)-1,2,4-oxadiazoles with DCC in the presence of KF/Al 2O3 and thiourea, is described. The structures of the new compounds were elucidated by spectroscopic and physical data, and the crystal structure determination by X-ray diffraction of three examples.