For the first time, amides and ureas based on both 5-nitroisoquinoline and 5-nitrosoisoquinoline were obtained by direct nucleophilic substitution of hydrogen in the 5-nitroisoquinoline molecule. In ...the case of urea and monosubstituted ureas, only 5-nitrosoisoquinoline-6-amine is formed under anhydrous conditions.
A meso-functionalization strategy has successfully been applied to the synthesis of novel 1,3,7-triazapyrene derivatives of calixarenes. The key synthetic step in these transformations providing the ...direct C–C bond formation is nucleophilic substitution of hydrogen (SNH) in 1,3,7-triazapyrene. General photophysical characteristics for these macrocyclic compounds, as well as features in emission properties upon addition of various metal cations have been elaborated. Studies using NMR spectroscopy have also shown a mutual effect of both calix4arene and 1,3,7-triazapyrene moieties on the coordination process. The complex stoichiometry and binding constants for Al3+ and Fe3+ guests have been explored with titration experiments.
Intramolecular heterocyclization reaction of 7-arylamino-8-nitrosoquinolines was used to obtain previously unknown pyrido2,3-
a
phenazine derivatives. The reaction was performed in refluxing acetic ...acid. The final products, including unsubstituted pyrido2,3-
a
phenazine, were obtained in good yields.
New coumarinyl(pyrrolyl)ethenes with a 1,3-thiazole bridge were synthesized. When irradiated at 365 nm, a hexatriene-cyclohexadiene rearrangement of the ring-opened form into a colored ...non-fluorescent ring-closed isomer occurs. The back reaction takes place when exposed to visible light at 540 nm. Furthermore, the compound with terminal 2,4-di-tert-butyl-6-hydroxybenzylidene receptor group represents a multifunctional sensor exhibiting selective chromogenic activity towards palladium(II) ions and CN− and F− anions. This probe interacts with Pd2+ cations with a noticeable naked eye effect - a change in the solution color from yellow to orange. The complexation stoichiometry is 1:1 and the detection limit was found to be 4.5 × 10−7 mol L−1. Similarly, CN− and F− anions cause a contrast naked eye effect with a change in the color of the solution from yellow to rose-red. For convenient detection of the above ions, test strips containing 4-(2-(2-(2,4-di-tert-butyl-6-hydroxybenzylidene)hydrazinyl)-5-(2-oxo-2H-chromen-3-yl)thiazol-4-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile have been developed. In addition, a combinatorial molecular logic gate was designed based on multi-controllable photoswitching properties of the obtained probe.
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•Photo- and ionocromic coumarinyl(pyrrolyl)ethenes with a 1,3-thiazole bridge were synthesized.•Test strips have been developed for easy detection of the Pd2+, CN− and F− ions.•A combinatorial molecular logic gate was designed based on multi-controllable photoswitching properties.
SNH Arylamination of 5-, 6-, 7-, and 8-nitroquinolines in anhydrous DMSO gave not only the arylamino derivatives of the respective nitroquinolines, but also the arylamino derivatives of ...nitrosoquinolines. In the case of 6-nitroquinoline, the first representatives of polycyclic structures on the basis of pyrido3,2-aphenazine 7-oxide were isolated.
A method has been developed for oxidative SNH alkyl carbamoyl amination of 3-nitropyridine in anhydrous DMSO. When anions of alkyl- and 1,1-dialkylureas were used as nucleophiles, an unusual ...formation of a mixture consisting of 1-alkyl(1,1-dialkyl)-3-(5-nitropyridin-2-yl)ureas and their nitroso analogs occurred, which was the first such observation with 3-nitropyridine. Only the nitro products formed in the presence of nitrobenzene. Additionally, a range of N-oxides were obtained on the basis of the synthesized compounds.
S.sub.N.sup.H Arylamination of 5-nitroquinoline N-oxides Pobedinskaya, Diana Yu; Demidov, Oleg P; Avakyan, Elena K ...
Chemistry of heterocyclic compounds (New York, N.Y. 1965),
05/2023, Letnik:
59, Številka:
4-5
Journal Article
Recenzirano
The corresponding arylamino derivatives were obtained by direct S.sub.N.sup.H arylamination of 5(6,7)-nitroquinoline N-oxides in anhydrous DMSO. 8-Nitroquinoline N-oxide underwent degradation under ...these conditions.
S.sub.N.sup.H Amidation of 5-nitroquinoline N-oxides Borovleva, Anastasia A; Avakyan, Elena K; Amangasieva, Gulminat A ...
Chemistry of heterocyclic compounds (New York, N.Y. 1965),
05/2022, Letnik:
58, Številka:
4-5
Journal Article
Recenzirano
Direct S.sub.N.sup.H amidation of 6- and 7-nitroquinoline N-oxides in anhydrous DMSO allowed to obtain N-oxides of 2- and 8-aroylaminonitroquinolines, respectively. 5-Nitroquinoline N-oxide was ...transformed into a mixture of amides derived from the N-oxides of 5-nitroand 5-nitrosoquinolines. 8-Nitroquinoline N-oxide underwent destruction under the same conditions.
A
-functionalization strategy has successfully been applied to the synthesis of novel 1,3,7-triazapyrene derivatives of calixarenes. The key synthetic step in these transformations providing the ...direct C-C bond formation is nucleophilic substitution of hydrogen (S
) in 1,3,7-triazapyrene. General photophysical characteristics for these macrocyclic compounds, as well as features in emission properties upon addition of various metal cations have been elaborated. Studies using NMR spectroscopy have also shown a mutual effect of both calix4arene and 1,3,7-triazapyrene moieties on the coordination process. The complex stoichiometry and binding constants for Al
and Fe
guests have been explored with titration experiments.
Arylamino derivatives of both the corresponding nitroquinolones and nitrosoquinolones were first obtained by direct nucleophilic substitution of hydrogen in the molecules of ...1-methyl-5(6,7,8)-nitroquinolin-2(1Ð)-ones.
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