Photosolvolysis of bridgehead quaternary ammonium salts. I. Synthesis of some 3-benzazonine derivatives

1984 ◽  
Vol 37 (6) ◽  
pp. 1203 ◽  
Author(s):  
JB Bremner ◽  
KN Winzenberg
Keyword(s):  
Ultraviolet Irradiation ◽  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Amino Ketone ◽  
Heterocyclic Derivative ◽  
Amino Aldehyde ◽  
Medium Ring

The medium-ring heterocyclic derivative 7,9,10-trimethoxy-3-methyl-2,3,4,5,6,7-hexahydro-1H-3- benzazonine (10a) was obtained from the ultraviolet irradiation of the reduced pyrrolo[2,1-aliso-quinolinium iodide salt (9a) in methanol, along with N-[2-(3,4-dimethoxypheny1)ethyl]-4,4-dimethoxy- N-methylbutan-1-amine (11a) and N-[2-(3,4-dimethoxyphenyl)ethyl]-2-methoxy-N-methylpyrrol-idinium iodide (13a). Analogous products were also obtained from the photolysis of 8,9-dimethoxy- 4-methyl-1,2,3,5,6,10b-(10b-D)hexahydropyrrolo[2,1-a]isoquinolinium iodide (9b) and 8,9-di-methoxy-4,10b-dimethyl-1,2,3,5,6,10b-hexahydropyrroo[2,-a]isoquinolinium iodide (9c), with the exception of no pyrrolidinium salt from the latter. Photolysis of (9a) and (9c) in water afforded the corresponding hexahydro-1H-3-benzazonin-7-ols (10d) and (10e), and the amino aldehyde (12a) and the amino ketone (12b) respectively.

Photosolvolysis of bridgehead quaternary ammonium salts. II. Synthesis of some 2,5-Benzoxazonine derivatives and attempted synthesis of the 1,2,4,5,6,7-Hexahydro-3,5-benzoxazonine system

1984 ◽  
Vol 37 (8) ◽  
pp. 1659 ◽  
Author(s):  
JB Bremner ◽  
KN Winzenberg
Keyword(s):  
Aromatic Ring ◽  
Ultraviolet Irradiation ◽  
Quaternary Ammonium ◽  
Potassium Hydroxide ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Heterocyclic Derivative ◽  
Medium Ring

The medium-ring heterocyclic derivative 1,9,10-trimethoxy-5-methyl-1,3,4,5,6,7-hexahydro-2,5- benzoxazonine (6a) was obtained in fair yield from photosolvolysis of 8,9-dimethoxy-4-methyl- 2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinolinium iodide (5a) in methanol, together with minor amounts of 3,9,10-trimethoxy-5-methy1-1,3,4,5,6,7-hexahydro-2,5-benzoxazonine (8) and 2-[N-2- {2-(dimethoxymethyl)-4,5-dimethoxyphenyl}ethyl-N-methylamino]ethanol (7). Photosolvolysis products analogous to (6a) were obtained from other related lob-substituted oxazolo[2,3-aliso-quinolinium iodides in high to low yields depending upon the nature of the angular substituent and the presence or absence of substituents in the fused aromatic ring. No methanolysis of the methiodide salts (5a-f) was observed in the absence of ultraviolet irradiation, whereas 1-(2-ethenyl- 4,s-dimethoxypheny1)ethanone (14) was formed on heating (5b) with methanolic potassium hydroxide. Attempted synthesis of 1,2,4,5,6,7-hexahydro-3,5-benzoxazonine derivatives by photosolvolysis of 8,9-dimethoxy-4-methyl-1,5,6,10b-tetrahydro-3H-oxazolo[4,3-a]isoquinolinium iodide (17) in methanol or water was unsuccessful, ring-opened products being obtained in low yield instead.

Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Anna Brol
Keyword(s):  
Phosphonic Acid ◽  
Quaternary Ammonium ◽  
Alkylating Agent ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Aminoalkylphosphonic Acid

An effective protocol for quaternization of simple 1-aminoalkylphosphonic acids under basic conditions and using Me2SO4 as convenient alkylating agent is reported. In the course of reaction phosphonic acid quaternary ammonium...

scholarly journals Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2424 ◽  
Author(s):  
Tăbăcaru ◽  
Botezatu ◽  
Horincar ◽  
Furdui ◽  
Dinică
Keyword(s):  
Escherichia Coli ◽  
Triticum Aestivum ◽  
Seed Germination ◽  
Quaternary Ammonium ◽  
Pathogenic Bacteria ◽  
Classical Method ◽  
Triticum Aestivum L ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Radicle Growth

A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 hours were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination.

Interaction of water-insoluble quaternary ammonium salts with the hydrated silica surface

1996 ◽  
Vol 32 (6) ◽  
pp. 331-334
Author(s):  
V. V. Turov ◽  
O. A. Zaporozhets ◽  
O. Yu. Nadzhafova ◽  
V. V. Sukhan
Keyword(s):  
Quaternary Ammonium ◽  
Silica Surface ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Hydrated Silica

Curare-like Action of Polymethylene bis-Quaternary Ammonium Salts

Nature ◽  
1948 ◽  
Vol 161 (4097) ◽  
pp. 718-718 ◽  
Author(s):  
R. B. BARLOW ◽  
H. R. ING
Keyword(s):  
Quaternary Ammonium ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts
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