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.
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.
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.
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.
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.
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.
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•C–N bond formation by direct oxidative nucleophilic substitution of hydrogen.•A new approach to synthesize 9-aminoacridine.•A new synthesis of 1-(acridin-9-yl)-3-alkyl(dialkyl)-ureas ...has been developed.
The ability of urea anions to react as nucleophiles with acridine has been investigated. An effective SNH synthesis of 9-aminoacridine was developed using the urea/NaH/DMSO system. However, when mono substituted ureas containing bulky substituents or 1,1-dialkyl substituted ureas were used, products of the SNH reaction of alkyl carbamoyl amination were obtained. Single crystal structure and the tautomerism of selected compound were studied.
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