scholarly journals Synthesis and properties of maleopimaric acid amides, imides and imidoamides with arylisoxazole and quinoline fragments

2021 ◽  
Vol 57 (4) ◽  
pp. 424-430
Author(s):  
M. P. Bei ◽  
A. P. Yuvchenko ◽  
V. I. Potkin ◽  
S. K. Petkevich
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Maleic Anhydride ◽  
1H Nmr ◽  
Acid Chloride ◽  
1H Nmr Spectroscopy ◽  
Rotatory Power ◽  
Biological Properties ◽  
Maleopimaric Acid ◽  
Chiral Lc

The method for maleopimaric acid N-(5-arylisoxazol-3-yl)amides synthesis has been developed by reaction of maleopimaric acid chloride with 3-amine-5-phenyl(4-methylphenyl)isoxazoles. N’-butyl-, N’-(2-hydroxyethyl)imides of maleopimaric acid N-(5-arylisoxazol-3-yl)amides were prepared. Heterocyclic imide – maleopimaric acid N-(quinolin-8-yl) imide was prepared by reaction of maleopimaric acid and 8-aminoquinoline in toluene at reflux in 97.1 % yield. It was established that refluxing of toluene solution of 8-aminoquinoline and maleated rosin, prepared by treatment of rosin with maleic anhydride and containing at least 50 % of maleopimaric acid, leads to the formation of maleopimaric acid N-(quinolin-8-yl)imide in 52.5 % yield (based on weight of maleated rosin). It was found by the methods of IR-, 1H NMR spectroscopy and mass-spectrometry that maleopimaric acid N-(quinolin-8-yl)imide consists of two diastereomeric atropisomers at 1:0.40 ratio. The biological properties of the prepared compounds were studied. It was established that maleopimaric acid N-(5-(4-methylphenyl)isoxazol-3-yl)amide possesses rotatory power (26 mkm-1) and may be used as chiral dopant to nematic LC for preparation of chiral LC-compositions.

scholarly journals CRYSTAL STRUCTURE AND TAUTOMERISM OF ALKYLAMINO-β-KETOENOLS IN SOLUTIONS

2019 ◽  
Vol 85 (8) ◽  
pp. 73-82
Author(s):  
VIKTOR CHERNII
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
1H Nmr ◽  
Trifluoroacetic Acid ◽  
1H Nmr Spectroscopy ◽  
Keto Group ◽  
Polymethine Chain ◽  
X Ray Diffraction ◽  
The Stability ◽  
Crystalline System

The structure of alkylamino-β-ketoenols obtained by opening of the pyran cycle of chalcones based on dehydracetic acid was studied by X-ray diffraction, IR, 1H NMR spectroscopy and chromatography-mass spectrometry. The infrared spectra of the compounds appear to be typical of β-ketoenols. The crystalline structure (2Z,5Z,7E,9E)-6-hydroxy-2-(methylami-no)-10-phenylethoxy-2,5,7,9-tetraene-4-one was first determined. A comparative analysis of it with 2 pre-viously published structures has been carried out. All of these compounds are crystallized in the form of yellow plates in the monoclinic crystalline system (spatial group P21/n), they have a planar arrangement of the polyene chain and β-ketoenol fragment con-jugated to the aromatic ring. It has been established that the planar configuration of the β-ketoenol fragment is stabilized by hydrogen bonds between the hydroxy and keto group and the amino and keto group in the crystalline state. The length of the polymethine chain, the nature of the substituents in the aromatic and aliphatic part of the molecule do not significantly affect the size and geometry of the alkylamino-β-ketoenolate fragment. Approximately the same lengths of bonds, the distance between atoms and the corners indicate that all these com-pounds may have similar chelating properties. Ac-cording to 1H NMR spectroscopy in various deu-terated solvents (benzene, DMSO, chloroform, ace-tone, methanol and trifluoroacetic acid), most of the main signals of the obtained compounds have sa-tellites, which indicates the existence of several isomeric forms in solutions. The analysis of integral intensities of labile protons in 1H NMR spectra does not allow to obtain accurate results regarding the ratio of tautomers in a solution, but for a series of compounds their approximate ratio in chloroform, DMSO and trifluoroacetic acid have been established (from 70:30 in CDCl3 to 90:10 in DMSO and CF3CO2D). The stability of the tautomers in the solutions is confirmed by the data of chromatogra-phy-mass spectrometry.

scholarly journals New Sulfamides Based on 1-Izopropil-3-α-Naftyl-5- Methoxymethyl-4-Aminopyrazole and Determination of Their Structure

2019 ◽  
pp. 405-412
Author(s):  
Ilya G. Povarov ◽  
Nikita A. Shilenkov ◽  
Ekaterina V. Neupokoeva ◽  
Ivan V. Peterson ◽  
Georgy A. Suboch ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
1H Nmr Spectroscopy ◽  
Reduction Reaction ◽  
Composition And Structure ◽  
Modern Methods ◽  
Derivatives Of

For the previously obtained 1-isopropyl-3-α-naphthyl-5-methoxymethyl-4-nitrosopyrazole, a reduction reaction with hydrazine hydrate was performed. It was first synthesized by 1-isopropyl-3-α-naphthyl- 5-methoxymethyl-4-aminopyrazole which was then sulfonylated by p-acetamidobenzenesulfonyl chloride and p-toluenesulfonic chloride. As a result previously unknown sulfonylated derivatives of N-alkylated aminopyrazoles were obtained. The composition and structure are confirmed by modern methods of analysis such as IR, 1H NMR spectroscopy and mass spectrometry

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