Antimicrobial and antiviral activity of pyridinium salts

7-Azoniafluorenone, SNAr-Reactions, Electrostatic Effects Various fluorosubstituted benzoylchlorides la -c are transformed into the corresponding acylpyridinium triflates 2a-c by one equivalent of the reagent pair 4-dimethyl-aminopyridine/trimethylsilyltriflate (DMAP/TMSOTf). Due to the combined electrostatic and mesomeric effect of the acylpyridinium function, fluorine substituents in oand p-positions can be subsequently substituted with a pyridinio group by additional equivalents of DMAP/ TMSOTf via an SNAr mechanism. Whereas the p-substitution product can be isolated as the highly electrophilic dication salt 3b, the corresponding mono-and bis-orthosubstituted polycation salts 3a and 3c are transformed under the reaction conditions to the 7-azoniafluorenone derivatives 4a,c by a novel cyclo-acylation. Structural and electrochemical data of these compounds are presented.

show abstract

“…Das nach Schema 1 leicht zugängliche Acyloniosalz 3b eröffnet einen einfachen Zugang zu phar mazeutisch wirksamen [27,28] …”

Section: Folgeuntersuchungen Am Dikationsalz 3bunclassified

7-Azoniafluorenonderivate durch elektrostatisch aktivierte S_NAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated S_NAr-Reactions

Weiß

Pühlhofer

Hampel

2001

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

show abstract

“…Diese Substanzklasse wurde durch die A rbeitsgruppen von D orofeenko und Supuran näher untersucht [18][19][20][21]. Analog zu den entsprechenden Benzamid-Derivaten [22][23] wa ren derartige Salze bislang nur durch Kondensa tion von Pyryliumsalzen mit 4-Amino-substituierten Benzolsulfonamiden darstellbar.…”

Section: Substitutionsreaktionen An 4-fluorbenzol-unclassified

“…Aufgrund der pharmazeutischen W irksamkeit (u.a. gegen H er pes simplex [18]) dieser Substanzklasse ist der in Schema 3 gezeigte einfache Zugang zu Verbindun gen dieses Typs von prinzipiellem Interesse.…”

Section: Substitutionsreaktionen An 4-fluorbenzol-unclassified

Elektrostatische Aktivierung der S_NAr-Reaktivität durch Sulfonyloniosubstituenten/Electrostatic Activation of S_NAr-Reactivity by Sulfonylonio Substituents

Weiß¹,

Pühlhofer²

2001

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

Electrostatic Effects, Polycations 4-Fluorobenzenesulfonyl chloride (1) and pentafluorobenzenesulfonyl chloride (2) are transformed into the corresponding N-sulfonylpyridinium triflates 4a-d by treatment with one equivalent of the reagent pair L/TMSOTf (L = 4-dimethylaminopyridine (DMAP), 4ferf-butylpyridine (TBUPY), 1-methylimidazole (NMI); TMSOTf = trimethylsilyl triflate). Due to the electrostatic effect of the sulfonylonio function, SNAr reactions on these systems can be performed under mild conditions. So the reaction of 2 with excess DMAP/TMSOTf leads by way of peronio substitution to hexakis[(4-dimethylamino)-l-pyridinio]benzene hexakis(trifluoromethansulfonate) (7) [22] at room temperature. Additionally, a new reaction path to 4-(l-pyridinio)-substituted benzenesulfonamides, a class of pharmaceutically interesting substances, is shown.

show abstract

Vibrational spectra, normal coordinate analysis, and hydrogen bond investigation of pyridinium perchlorate

Omidvar

Tayyari

Vakili

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

View full text Add to dashboard Cite

Antimicrobial and antiviral activity of pyridinium salts

Cited by 3 publications

References 2 publications

7-Azoniafluorenonderivate durch elektrostatisch aktivierte S_NAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated S_NAr-Reactions

7-Azoniafluorenonderivate durch elektrostatisch aktivierte S_NAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated S_NAr-Reactions

Elektrostatische Aktivierung der S_NAr-Reaktivität durch Sulfonyloniosubstituenten/Electrostatic Activation of S_NAr-Reactivity by Sulfonylonio Substituents

Vibrational spectra, normal coordinate analysis, and hydrogen bond investigation of pyridinium perchlorate

Contact Info

Product

Resources

About

Antimicrobial and antiviral activity of pyridinium salts

Cited by 3 publications

References 2 publications

7-Azoniafluorenonderivate durch elektrostatisch aktivierte SNAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated SNAr-Reactions

7-Azoniafluorenonderivate durch elektrostatisch aktivierte SNAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated SNAr-Reactions

Elektrostatische Aktivierung der SNAr-Reaktivität durch Sulfonyloniosubstituenten/Electrostatic Activation of SNAr-Reactivity by Sulfonylonio Substituents

Vibrational spectra, normal coordinate analysis, and hydrogen bond investigation of pyridinium perchlorate

Contact Info

Product

Resources

About

7-Azoniafluorenonderivate durch elektrostatisch aktivierte S_NAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated S_NAr-Reactions

7-Azoniafluorenonderivate durch elektrostatisch aktivierte S_NAr-Reaktionen / 7-Azoniafluorenone Derivatives by Electrostatically Activated S_NAr-Reactions

Elektrostatische Aktivierung der S_NAr-Reaktivität durch Sulfonyloniosubstituenten/Electrostatic Activation of S_NAr-Reactivity by Sulfonylonio Substituents