One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Using Catalytic System NaOH‒DMSO

Pankrat'eva, Vitalina; Sharonova, Tatyana; Tarasenko, M. V.; Baikov, S. V.; Кофанов, Е. Р.

doi:10.1134/s1070428018080213

Cited by 21 publications

(12 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The original approach to the synthesis of 1,2,4-oxadiazoles 3a-g and 5a-q has been previously described by our group (for more information see Supplementary Material) [9,18,19,20,21], and the four newly prepared compounds 3h and 5r-t were obtained in the similar manner (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

Shetnev

Baykov

Kalinin

et al. 2019

IJMS

View full text Add to dashboard Cite

Replacement of amide moiety with the 1,2,4-oxadiazole core in the scaffold of recently reported efflux pump inhibitors afforded a novel series of oxadiazole/2-imidazoline hybrids. The latter compounds exhibited promising antibacterial activity on both Gram-positive (Staphylococcus aureus, Bacillus subtilis) and Gram-negative (Escherichia coli, Pseudomonas fluorescens) strains. Furthermore, selected compounds markedly inhibited the growth of certain drug-resistant bacteria. Additionally, the study revealed the antiproliferative activity of several antibacterial frontrunners against pancreas ductal adenocarcinoma (PANC-1) cell line, as well as their type-selective monoamine oxidase (MAO) inhibitory profile.

show abstract

Section: Resultsmentioning

confidence: 99%

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

Shetnev

Baykov

Kalinin

et al. 2019

IJMS

View full text Add to dashboard Cite

show abstract

“…General procedure for the preparation of 3, 4, 6. The solution of triethylamine (0.75 mmol, 104 μL) in 1,2-DCE (5 mL) was added to mixture of oxadiazolone (1 or 5, 0.5 mmol, prepared by slightly modified reported procedures), [71,72] diaryliodonium salt (2, 0.75 mmol) and CuI (10 mol%, 9.5 mg) under Ar atmosphere. The resulted mixture was heated at 60°C for 24 hours.…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts

et al. 2021

View full text Add to dashboard Cite

Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N-and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol.

show abstract

“…General procedure for the preparation of 3, 4, 6. The solution of triethylamine (0.75 mmol, 104 µL) in 1,2-DCE (5 mL) was added to mixture of oxadiazolone (1 or 5, 0.5 mmol, prepared by slightly modified reported procedures), [54,55] diaryliodonium salt (2, 0.75 mmol) and CuI (10 mol%, 9.5 mg) under Ar atmosphere. The resulted mixture was heated at 60 °C for 24 hours.…”

Section: Experimental Partmentioning

confidence: 99%

Copper-Catalyzed Selective Arylation of Oxadiazolones by Diaryliodonium Salts

Soldatova¹,

Semenov²,

Geyl³

et al. 2021

Preprint

View full text Add to dashboard Cite

The direct N-arylation of cyclic amides can be considered a pivotal issue for modern organic chemistry. Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts in mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows to efficiently utilize both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). The evaluation of steric effects in aryl moieties to the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones exhibited the high potential of mesityl-substituted diaryliodonium salts as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol.

show abstract

One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Using Catalytic System NaOH‒DMSO

Cited by 21 publications

References 30 publications

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer

Copper‐Catalyzed Selective N‐Arylation of Oxadiazolones by Diaryliodonium Salts

Copper-Catalyzed Selective Arylation of Oxadiazolones by Diaryliodonium Salts

Contact Info

Product

Resources

About