Quantum-chemical description of the recyclization reactions of quaternary pyridinium salts

1979 ◽  
Vol 15 (11) ◽  
pp. 1201-1204 ◽  
Author(s):  
Yu. B. Vysotskii ◽  
B. P. Zemskii ◽  
T. V. Stupnikova ◽  
R. S. Sagitullin ◽  
A. N. Kost ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Pyridinium Salts ◽  
Quaternary Pyridinium Salts ◽  
Chemical Description

Sterically Crowded Heterocycles. IX. New α,β-Unsaturated Ketones Containing Imidazo[1,2-a]quinoline, Imidazo[2,1-a]isoquinoline, Benzo[h]imidazo[1,2-a]quinoline and Imidazo[1,2-a]-1,10-phenanthroline Moieties

1997 ◽  
Vol 62 (10) ◽  
pp. 1599-1611 ◽  
Author(s):  
Stanislav Böhm ◽  
Tomáš Strnad ◽  
Iveta Ruppertová ◽  
Josef Kuthan
Keyword(s):  
Quantum Chemical ◽  
Pyridinium Salts ◽  
Energy Data ◽  
Axial Chirality ◽  
Unsaturated Ketones ◽  
Pm3 Method ◽  
Quaternary Pyridinium Salts

(Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]heteroaryl)prop-2-en-1-ones 2-6 and isomeric [1-heteroaryl-3,5-diphenylpyrrol-2-yl]phenylmethanones 17-20 were prepared by the ferricyanide oxidation of quaternary pyridinium salts 12-16. Axial chirality and helicity of the molecules of 4 and 6 are discussed using various energy data obtained by the quantum chemical PM3 method.

A new heterocyclic ring closure in ferricyanide oxidation of 2,4,6-triphenylpyridinium salts

1983 ◽  
Vol 48 (11) ◽  
pp. 3307-3314 ◽  
Author(s):  
Petr Nesvadba ◽  
Petr Štrop ◽  
Josef Kuthan
Keyword(s):  
Alkaline Solution ◽  
Heterocyclic Ring ◽  
Potassium Ferricyanide ◽  
Probable Mechanism ◽  
Ring Closure ◽  
Pyridinium Salts ◽  
Mechanism Of Formation ◽  
Pyrrole Derivatives ◽  
Quaternary Pyridinium Salts ◽  
Heterocyclic Derivatives

The quaternary pyridinium salts Ia-Ic react with alkaline solution of potassium ferricyanide to give the condensed heterocyclic derivatives IIIa, b, IV, whereas the salts Id-If give the pyrrole derivatives IIa-IIc under the same conditions. The diaza heterocycle IIIa reacts with methyl iodide to give methoiodide V, whereas by action of bromine it produces two monobromo derivatives VIa, b. The pyrrole derivatives IIa, b give monobromo derivatives IId, e on bromination. A probable mechanism of formation of the heterocyclic derivatives is discussed.

Sterically Crowded Heterocycles. III. A General Approach to Imidazo[1,2-a]pyridines by Ferricyanide Oxidation of Quaternary Pyridinium Salts

1996 ◽  
Vol 61 (1) ◽  
pp. 126-138 ◽  
Author(s):  
Richard Kubík ◽  
Stanislav Böhm ◽  
Iveta Ruppertová ◽  
Josef Kuthan
Keyword(s):  
Potassium Hydroxide ◽  
Potassium Ferricyanide ◽  
Pyridinium Salts ◽  
Oxidizing Agents ◽  
Quaternary Pyridinium Salts ◽  
Substituted 1

Substituted 1-(pyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 1b-1e were converted with potassium ferricyanide and potassium hydroxide to sterically crowded 2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridines 2b-2e accompanied by minor isomeric 2-benzoyl-3,5-diphenyl-1-(pyridin-2-yl)pyrroles 3c-3e. 4-Phenyl-2,6-di(4-substituted phenyl)-1-(pyridin-2-yl)pyridinium salts 4a, 4b gave exclusively corresponding imidazo[1,2-a]pyridines 5a, 5b while the ferricyanide oxidation of 1-(5-iodo- and 5-cyanopyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 6a, 6b led to mixtures of major imidazo[1,2-a]pyridines 7a-7c and minor pyrroles 8a-8c. Some mechanistic aspects of the oxidation procedure are discussed in connection with a resistance of 2,6-diphenyl-1,3,5-trimethylpyridinium perchlorate (9c) towards the oxidizing agents.

Effect of micelle formation of quaternary pyridinium salts on their recyclization to anilines

1981 ◽  
Vol 17 (4) ◽  
pp. 367-369 ◽  
Author(s):  
T. V. Stupnikova ◽  
A. I. Serdyuk ◽  
V. N. Kalafat ◽  
R. S. Sagitullin ◽  
V. P. Marshtupa
Keyword(s):  
Micelle Formation ◽  
Pyridinium Salts ◽  
Quaternary Pyridinium Salts
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