Nitrosylsulfuric acid as an oxidant in the synthesis of 3,5-diarylisoxazoles

2018 ◽  
Vol 67 (3) ◽  
pp. 517-520 ◽  
Author(s):  
O. B. Bondarenko ◽  
A. I. Komarov ◽  
L. I. Kuznetsova ◽  
S. N. Nikolaeva ◽  
A. Yu. Gavrilova ◽  
...  
Keyword(s):  
Nitrosylsulfuric Acid

Nitrosylsulfuric Acid

2001 ◽  
Author(s):  
George A. Olah ◽  
G. K. Surya Prakash ◽  
Qi Wang ◽  
Xing-Ya Li
Keyword(s):  
Nitrosylsulfuric Acid

Transformation of 2-alkylamino-1,4-naphthoquinones into 2-alkylnaphtho[2,1-d][1,3]oxazole-4,5-dione 4-oximes by the action of nitrosylsulfuric acid

2014 ◽  
Vol 50 (12) ◽  
pp. 1814-1820 ◽  
Author(s):  
L. M. Gornostaev ◽  
Yu. G. Khalyavina ◽  
T. I. Lavrikova ◽  
Yu. V. Gatilov ◽  
G. A. Stashina ◽  
...  
Keyword(s):  
Nitrosylsulfuric Acid

Nitrosylsulfuric acid as a tandem reagent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes

2019 ◽  
Vol 68 (6) ◽  
pp. 1200-1203
Author(s):  
O. B. Bondarenko ◽  
A. I. Komarov ◽  
G. L. Karetnikov ◽  
S. N. Nikolaeva ◽  
N. V. Zyk
Keyword(s):  
Nitrosylsulfuric Acid

On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid

2019 ◽  
Vol 55 (5) ◽  
pp. 608-614
Author(s):  
L. M. Gornostaev ◽  
E. V. Nuretdinova ◽  
T. I. Lavrikova ◽  
Yu. G. Khalyavina ◽  
O. I. Fominykh ◽  
...  
Keyword(s):  
Nitrosylsulfuric Acid

Modellreaktionen zur Plumbagin-Synthese, 2. Mitteilung 5-Amino-1-naphthol als Startkomponente / Model Reactions for Plumbagin Synthesis, 2nd Communication 5-Amino-1-naphthol as Starting Compound

1987 ◽  
Vol 42 (12) ◽  
pp. 1578-1584 ◽  
Author(s):  
Hans Möhrle ◽  
Hubertus Folttmann
Keyword(s):  
Hydroxy Group ◽  
Mannich Bases ◽  
Starting Compound ◽  
Derivatives Of ◽  
Nitrosylsulfuric Acid ◽  
Model Reactions

AbstractThe aminomethylation of 5-amino-1-naphthol (1) and 5-acetamido-1-naphthol (9) is examined. While the hydrogenolysis of the phenol Mannich bases derived from 1 cannot be accomplished, the derivatives of 9 react easily. The oxidation of the 2-methylphenol compounds 5 and 18 to the corresponding quinones may performed with Fremy's salt. The following transforming of the amino to the hydroxy group by nitrosylsulfuric acid succeeds with small yield only.

Studies of the acylarylnitrosamine reaction. I. The use of nitrosylsulfuric acid in the preparation of unsymmetrical biaryls

1967 ◽  
Vol 45 (13) ◽  
pp. 1539-1542 ◽  
Author(s):  
Yusuf Ahmad ◽  
M. Ikram Qureshi ◽  
M. Ibrahim Baig
Keyword(s):  
Pure State ◽  
Room Temperature ◽  
Nitrosylsulfuric Acid

Nitrosylsulfuric acid, which is very easy to prepare in a pure state and is quite stable at room temperature, has been found to be a very suitable reagent for the nitrosation of acylarylamines. The nitroso derivatives can be isolated easily, and on decomposition in benzene have yielded unsymmetrical biaryls in improved yields. Some of the nitrosations that could not be achieved earlier have now been accomplished successfully by this method.

scholarly journals Synthesis of 5-hydroxy-10-R-benzo[a]phenazine-12-oxides by cyclization of 2-arylamino-1,4-naphthoquinone-1-oximes under the action of nitrating mixture

2020 ◽  
Vol 61 (2) ◽  
pp. 12-23
Author(s):  
Leonid M. Gornostaev ◽  
Keyword(s):  
Acetic Acid ◽  
Biological Activity ◽  
Nitrogen Oxide ◽  
Biologically Active ◽  
Alkyl Aryl ◽  
High Biological Activity ◽  
Fine Organic Synthesis ◽  
Wide Range ◽  
Fine Organic ◽  
Nitrosylsulfuric Acid

The synthesis of рolycyclic quinoid compounds, which exhibit a wide range of biological activity is one of the most promising and actively developing areas of the fine organic synthesis. Heterocyclic compounds including those that can be donors of nitrogen oxide NO occupy a special place among biologically active structures. These substances include a number of N-oxides, e.g., 1,2-diazet-1,2-dioxides, furoxanes and their benzo analogs, and N,N′-pyrazole dioxides. The reason for the high biological activity of N-oxides of nitrogenous heterocycles, which cannot easily generate nitrogen oxide NO may be their oxidative properties. Thus, N-oxides of nitrogenous heterocycles are of interest due to their high biological activity. We have developed an approach to the synthesis of 5-hydroxy-10-R-benzo[a]phenazine-12-oxides that contain the N-oxide fragment, which makes these compounds promising for studying their biological activity. We have demonstrated that the treatment of 2-arylamino-1,4-naphthoquinones with hydroxylamine in ethanol at 50-60 °С leads to selective oximation at position 1 and the formation of 2-arylamino-1,4-naphthoquinone-1-oximes. It has been shown that the interaction of 2-arylamino-1,4-naphthoquinone-1-oximes with the nitrating mixture in acetic acid results in the formation of 5-hydroxy-10-R-benzo[a]phenazine-12-oxides. Our work is a continuation of the study on the interactions of 2-arylamino-1,4-naphthoquinones and 4-arylamino-1,2-naphthoquinones with nitrosylsulfuric acid in acetic acid and the interaction of 2-alkyl(benzyl)amino-1,4-naphthoquinones with nitrosylsulfuric acid or nitrating mixture in acetic acid. The former reactions lead to the formation of 3-R-benzo[b]phenazine-6,11-dione-5-oxides and 9-R-benzo[a]phenazine-5,6-dion-7-oxides, respectively. The latter reaction leads to the formation of 2-alkyl(aryl)naphtho[2,1-d][1,3]oxazole-4,5-dione-4-oximes and 2-alkyl(aryl)-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-dione as main products.

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