Synthesis of phenethanolamine derivatives with potential β-adrenergic antagonistic activity

1975 ◽  
Vol 28 (5) ◽  
pp. 1023 ◽  
Author(s):  
SJ Pasaribu ◽  
LR Williams
Keyword(s):  
Magnetic Resonance ◽  
Ring Opening ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Antagonistic Activity ◽  
Spectral Studies ◽  
Aryl Ring ◽  
Mass Spectral

The mass spectra of bromonitroacetophenones, intermediates in the synthesis of phenethanolamine derivatives containing a nitro and bromo group in the aryl ring, have been studied. The acetophenones were converted into the corresponding α,β-epoxystyrenes, which were then treated with various amines, and proton magnetic resonance and mass spectral studies were used to confirm the direction of ring opening and purity of the products.

STEROIDS AND RELATED NATURAL PRODUCTS. XXV PHOTOCHEMICAL TRANSFORMATION OF 3β-NITRITO-5α-LANOSTANE

1965 ◽  
Vol 43 (10) ◽  
pp. 2872-2878
Author(s):  
George R. Pettit ◽  
Raymond E. Kadunce ◽  
Paul. Sunder-Plassmann ◽  
John. Occolowitz
Keyword(s):  
Magnetic Resonance ◽  
Ultraviolet Irradiation ◽  
Photochemical Reaction ◽  
Proton Magnetic Resonance ◽  
Reaction Pathway ◽  
Spectral Studies ◽  
Photochemical Transformation ◽  
Photolysis Product ◽  
Mass Spectral ◽  
Phenylhydrazone Derivatives

Ultraviolet irradiation of 3β-nitrito-5α-lanostane was found to follow an unusual reaction pathway and yield 2-oximo-3-oxo-3,4-seco-5α-lanostane (IV). The new aldehyde was easily converted to oxime and phenylhydrazone derivatives. Acetylating the photolysis product led to an oxime acetate (IX) which readily rearranged to 1-cyano-3,4-seco-5α-lanostane (III). Confirmation for the structural assignments was obtained from a series of proton magnetic resonance and mass spectral studies. Application of the new photochemical reaction was suggested to preparation of certain aldehydes otherwise accessible only with difficulty.

scholarly journals Spectrometric Study of the Nitrile-Ketenimine Tautomerism

2009 ◽  
Vol 2009 ◽  
pp. 1-18 ◽  
Author(s):  
Hebe Saraví Cisneros ◽  
Sergio Laurella ◽  
Danila L. Ruiz ◽  
Agustín Ponzinibbio ◽  
Patricia E. Allegretti ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Mass Spectrum ◽  
Magnetic Resonance ◽  
Mass Spectra ◽  
Spectrometric Study ◽  
Mass Spectral ◽  
Ion Fragmentation ◽  
Nuclear Magnetic Resonance Spectra ◽  
Amination Product

Mass spectrometry is used to evaluate the occurrence of the nitrile-ketenimine tautomerism. Mass spectra of two differently substituted nitriles, ethyl-4,4-dicyano-3-methyl-3-butenoate and diethyl-2-cyano-3-methyl-2-pentenodiate are examined looking for common mass spectral behaviors. Ion fragmentation assignments for specific tautomers allow to predict the presence of the corresponding structures. Additionally, the mass spectrum and nuclear magnetic resonance spectra of ethyl-4,4-dicyano-2,2-diethyl-3-methyl-3-butenoate and that of the corresponding amination product support the occurrence of the ketenimine tautomer in the equilibrium.

Solvent effects in ultraviolet spectral studies of hydrogen bonding between phenol and N,N-dimethylacetamide

1967 ◽  
Vol 45 (18) ◽  
pp. 2033-2038 ◽  
Author(s):  
F. Takahashi ◽  
W. J. Karoly ◽  
J. B. Greenshields ◽  
N. C. Li
Keyword(s):  
Hydrogen Bonding ◽  
Magnetic Resonance ◽  
Complex Formation ◽  
Equilibrium Constant ◽  
Proton Magnetic Resonance ◽  
Mixed Solvent ◽  
Resonance Method ◽  
Spectral Studies ◽  
Magnetic Resonance Method ◽  
Hydrogen Bonded

Ultraviolet spectral studies of hydrogen bonding between phenol and N,N-dimethylacetamide (DMA) in several media are reported. The equilibrium constant for the formation of the phenol–DMA complex is strongly solvent dependent, varying from 295 1/mole in cyclohexane to 130 in CCl4 and 16 in CHCl3, all at 28°. The greatly reduced value in CHCl3 indicates that the measured equilibrium constant is only an apparent one which does not take into account the decrease in free DMA concentration resulting from hydrogen-bonded complex formation with the solvent acting as hydrogen donor. In CCl4/CHCl3 mixed solvent, in the range of [chloroform] = 0 to 1.227 M, the measured equilibrium constant, K′, varies linearly with K′ [chloroform]. The slope of the line corresponds to the equilibrium constant for the formation of the hydrogen-bonded complex between CHCl3 and DMA in CCl4. The value, 0.9 1/mole, agrees with that obtained from a proton magnetic resonance method. The agreement is particularly noteworthy when we consider that the concentrations of phenol used in the proton magnetic resonance and ultraviolet spectral methods differ by a factor of 200, which leads definitely to the conclusion that the hydrogen-bonded CHCl3–DMA complex formed is 1:1. In cyclohexane/CHCl3 mixed solvent, similar results are obtained.

CARCINOGENICITY OF LACTONES: I. THE REACTION OF 4-METHYLBUTENO- AND 4-METHYLBUTANO-γ-LACTONES WITH PRIMARY AMINES

1966 ◽  
Vol 44 (9) ◽  
pp. 1059-1068 ◽  
Author(s):  
J. Bryan Jones ◽  
John M. Young
Keyword(s):  
Magnetic Resonance ◽  
Michael Addition ◽  
Ring Opening ◽  
Proton Magnetic Resonance ◽  
Mechanisms Of Action ◽  
Reaction Pathways ◽  
Nucleophilic Attack ◽  
Primary Amines ◽  
Acid Lactone ◽  
The Michael Addition

As the first stage in the investigations of the mechanisms of action of carcinogenic lactones, the reactions of 4-hydroxypent-2-enoic acid lactone (II, R = CH3), which is a carcinogen, and of the non-carcinogenic 4-hydroxypent-3-enoic (III, R = CH3) and 4-hydroxypentanoic (IV, R = CH3) acid lactones with methylamine and benzylamine have been studied. As expected, the carcinogenic lactone reacts to give the Michael addition products, whereas both inactive lactones undergo ring opening by nucleophilic attack at the carbonyl group. From the relative rates of reaction of the amines with the lactones it is concluded that the induction of tumors by II (R = CH3) does not involve alkylation of biological primary alkylamino groups. The proton magnetic resonance spectra of the products enable the different reaction pathways to be distinguished readily, and may provide the basis for rapid physicochemical screening of alkylation agents that are potential carcinogens.

Mass spectra and proton magnetic resonance spectra of some tetrahydroprotoberberine alkaloids

1968 ◽  
Vol 46 (15) ◽  
pp. 2501-2506 ◽  
Author(s):  
C.-Y. Chen ◽  
D. B. MacLean
Keyword(s):  
Magnetic Resonance ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Structural Studies ◽  
New Members ◽  
Magnetic Resonance Spectra

The mass spectra and the proton magnetic resonance spectra of tetrahydroprotoberberine alkaloids, oxygenated at the 9- and 10-positions, show marked differences from the spectra of those oxygenated at the 10- and 11-positions. These differences may be useful in structural studies on new members of this group of alkaloids.

Proton magnetic resonance and mass spectrometric studies on derivatives of sodium 2-O-α-D-mannopyranosyl-D-glycerate and related compounds

1969 ◽  
Vol 47 (21) ◽  
pp. 4083-4086 ◽  
Author(s):  
J. N. C. Whyte
Keyword(s):  
Magnetic Resonance ◽  
Methyl Ester ◽  
Proton Magnetic Resonance ◽  
Mass Spectra ◽  
Red Alga ◽  
Mass Spectrometric ◽  
Derivatives Of ◽  
Related Compounds

The proton magnetic resonance (p.m.r.) and mass spectra of the methyl ester pentaacetate of sodium 2-O-α-D-mannopyranosyl-D-glycerate from the red alga Rhodomela larix are compared to those of related compounds to affirm the assigned structure.

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