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.
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.
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.