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 convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SN H), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with ...carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SN H transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.
SNH Arylamination of 5(6,7,8)-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
N
H
arylamination of 5(6,7)-nitroquinoline
N
-oxides in anhydrous DMSO. 8-Nitroquinoline
N
-oxide underwent degradation under these ...conditions.
A simple and efficient arylamination reaction of 5-nitroisoquinoline based on the oxidative nucleophilic substitution of hydrogen was demonstrated under metal-catalyst-free conditions. This reaction ...can be used as a method for the synthesis of isoquinoline-based diarylamines containing a nitroso group in the
ortho
position, which are compounds with high synthetic potential. The oxidation of the latter leads to the formation of 6-arylamino-5-nitroisoquinoline
N
-oxides. The absence of the need to introduce leaving groups and a good overall yield are features of this reaction.
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.
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.
The review summarizes data on the practical aspects of the interaction of nucleic acids with diazapyrene derivatives. The information on biological activity is given and the probable mechanisms ...underlying the action of diazapyrenes are analyzed. It contains 119 references.
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(1
Н
)-ones.
SNH Amidation of 5(6,7,8)-nitroquinoline N-oxides Borovleva, Anastasia A.; Avakyan, Elena K.; Amangasieva, Gulminat A. ...
Chemistry of heterocyclic compounds (New York, N.Y. 1965),
2022/5, Letnik:
58, Številka:
4-5
Journal Article
Recenzirano
Direct S
N
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.
The stable adducts,
N
-(1-methyl-5(6,7,8)-nitro-1,2-dihydroquinolin-2-yl)benzamides were synthesized for the first time by the action of amide anions of aromatic acids on the
N
-methyl salts of 5-, ...6-, 7-, and 8-nitroquinolines in anhydrous MeCN. Oxidative dehydrogenation of these amides afforded aroylimino derivatives of the corresponding 1-methyl-5(6,7,8)-nitro-2-quinolones.
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