A new method for the synthesis of n-(2-aminoethyl)azoles by alkylation of azoles with 2-alkyl-4,5-dihydrooxazoles

Попков, С. В.; Skvortsova, M. N.

doi:10.1007/s11172-006-0496-4

Cited by 3 publications

(12 citation statements)

References 10 publications

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“…Further, addition of 0.5 equiv of sodium hydride to boost the nucleophilicity and heating up to 150 °C for six hours did not provide any ring-opened product either. The same phenomenon was observed for another electron-poor substrate 2-(pyridin-4-yl)-2-oxazoline (14), derived from isonicotinic acid. The aforementioned observations are readily explained by invoking the intermediacy of protonated oxazoline 1′ (vide infra, Scheme 4).…”

supporting

confidence: 74%

“…For instance, imidazole was used to open the oxazoline ring, 14 as was azide in form of TMS-N 3 . 15 In the presence of a Brønsted-Lowry or Lewis acid, amines such as diphenylamine bring about a nucleophilic ring-opening of 2-ethyl-2-oxazoline (3) at high temperature (180 °C), offering a synthesis of unsymmetrically substituted ethylenediamines such as 4.…”

Section: Nuc: N H O Nucmentioning

confidence: 99%

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Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles

Gutiérrez¹,

Dean²,

Laxamana³

et al. 2016

Arkivoc

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Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl-and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.

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supporting

confidence: 74%

Section: Nuc: N H O Nucmentioning

confidence: 99%

Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles

Gutiérrez¹,

Dean²,

Laxamana³

et al. 2016

Arkivoc

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“…12 To prepare the aminoethylimidazole dihydrochloride salt (12), the corresponding 2-(2-(1Himidazol-1-yl)ethyl)isoindoline-1,3-dione (11) was required. The isoindoline-1,3-dione was prepared by following the procedure of Popkov and Skvortsova, 13 which involved melted imidazole refluxed with bromoethylphthalamide (10) and potassium iodide, resulting in the desired product (11) in 49% yield after recrystallization from isopropanol. The isoindole-1,3-dione was then treated with hydrazine following the Ing−Manske procedure to give the required aminoethylimidazole dihydrochloride (12) in 82% yield (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The final amides (13) were prepared by a carbonyldiimidazole (CDI) coupling reaction through the coupling of the carboxylic acids (9) with the free amine, generated in situ by the treatment of the aminoethylimidazole dihydrochloride salt (13) with triethylamine in DMF. The final amide derivatives (13) were obtained in low to moderate yields (Scheme 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The amide imidazole compounds (13) were positioned in a similar manner (Figure 4C) to 7 and 8. However, whereas imidazole (7) and triazole (8) were consistently positioned within the active site, numerous conformations were observed for the amide imidazole series (13), possibly owing to their increased conformational flexibility, which may correlate with the moderate binding affinity observed.…”

Section: Journal Of Medicinal Chemistrymentioning

confidence: 99%

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Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation

et al. 2017

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Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short −CH2– linker displayed promising antimycobacterial activity, with the imidazole–CH2– series (7) showing low MIC values (6.25–25 μg/mL), which was also influenced by lipophilicity. Extending the linker to −C(O)NH(CH2)2– resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV–visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.

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