Purely Aliphatic Azoxy Compounds with a Methyl Group attached to the Nitrogen Atom

Nature ◽  
1951 ◽  
Vol 167 (4256) ◽  
pp. 863-864 ◽  
Author(s):  
J. G. ASTON ◽  
D. M. JENKINS
Keyword(s):  
Nitrogen Atom ◽  
Methyl Group ◽  
Azoxy Compounds

Dirhodium-Catalyzed Chemo- and Site-Selective C–H Amidation of N,N-Dialkylanilines

Synlett ◽  
2020 ◽  
Author(s):  
Yoshihiro Ueda ◽  
Gong Chen ◽  
Kenta Arai ◽  
Kazuhiro Morisaki ◽  
Takeo Kawabata
Keyword(s):  
Nitrogen Atom ◽  
Aromatic Ring ◽  
Methyl Group ◽  
Site Selective

AbstractA method for dirhodium-catalyzed C(sp3)–H amidation of N,N-dimethylanilines was developed. Chemoselective C(sp3)–H amidation of N-methyl group proceeded exclusively in the presence of C(sp2)–H bonds of the electron-rich aromatic ring. Site-selective C(sp3)–H amidation proceeded exclusively at the N-methyl group of N-methyl-N-alkylaniline derivatives with secondary, tertiary, and benzylic C(sp3)–H bonds α to a nitrogen atom.

scholarly journals Synthesis and spectral characterization of novel 1,5-benzodiazepine oxime derivatives

2019 ◽  
Vol 84 (4) ◽  
pp. 343-353
Author(s):  
Lina Rekovic ◽  
Lidija Kosychova ◽  
Irina Bratkovskaja ◽  
Regina Vidziunaite
Keyword(s):  
Nitrogen Atom ◽  
Fluorescence Spectroscopy ◽  
Organic Solvent ◽  
Elemental Analysis ◽  
13C Nmr ◽  
1H And 13C Nmr ◽  
Methyl Group ◽  
Oxime Derivatives ◽  
New Compounds

Three new 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one oximes were synthesized and characterized by the methods of 1H- and 13C-NMR, IR and elemental analysis. Along with previously described compounds bearing one additional methyl group on the 5th nitrogen atom, the new compounds were characterized in bulk by UV?Vis and fluorescence spectroscopy in various solvents. The influence of the nature of the organic solvent on the spectra of the title compounds was investigated and is discussed.

scholarly journals Isolation of two N-monosubstituted protoporphyrins, bearing either the whole drug or a methyl group on the pyrrole nitrogen atom, from liver of mice given griseofulvin

1991 ◽  
Vol 274 (3) ◽  
pp. 843-848 ◽  
Author(s):  
A E Holley ◽  
Y Frater ◽  
A H Gibbs ◽  
F De Matteis ◽  
J H Lamb ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Protoporphyrin Ix ◽  
Secondary Product ◽  
Structural Isomers ◽  
Green Pigment ◽  
Methyl Group ◽  
Group 4 ◽  
Pyrrole Nitrogen

1. A hepatic green pigment with inhibitory properties towards the enzyme ferrochelatase has been isolated from the liver of mice treated with griseofulvin and identified as N-methylprotoporphyrin. 2. All four structural isomers of N-methylprotoporphyrin have been demonstrated to be present, NA, where ring A of protoporphyrin IX is N-methylated, being the predominant isomer. 3. In addition to N-methylprotoporphyrin, a second green pigment, present in far greater amounts, was also isolated from the liver of griseofulvin-treated mice. This second green pigment is also an N-monosubstituted protoporphyrin, but in this case the substituent on the pyrrole nitrogen atom appears to be intact griseofulvin rather than a methyl group. 4. The fragmentation of this adduct in tandem m.s. studies suggests that griseofulvin is bound to the pyrrole nitrogen through one of its carbon atoms and further suggests that N-methylprotoporphyrin may arise as a secondary product from the major griseofulvin pigment.

Kinetics of acid-catalyzed cyclization of substituted hydantoinamides to substituted hydantoins

1987 ◽  
Vol 52 (8) ◽  
pp. 1999-2004 ◽  
Author(s):  
Jaromír Kaválek ◽  
Vladimír Macháček ◽  
Gabriela Svobodová ◽  
Vojeslav Štěrba
Keyword(s):  
Hydrogen Atom ◽  
Nitrogen Atom ◽  
Hydrochloric Acid ◽  
Dissociation Constants ◽  
Amide Group ◽  
The Other ◽  
Methyl Group ◽  
Acid Catalyzed ◽  
Cyclization Rate ◽  
Kinetics Of

The kinetics of acid-catalyzed cyclization of the hydantoinamides type R3-N(5)H-CO-N(3)R2-CH2-CO-N(1)HR1 (R1, R2, R3 = H and/or CH3) has been studied in 0·5 to 5 mol l-1 hydrochloric acid. The cyclization rate is limited by the rate of the attack of nitrogen atom N(5) on the carbon atom of the protonated amide group. The dissociation constants of the protonated hydantoinamides and rate constants of their cyclizations have been determined. Replacement of hydrogen atom by methyl group at the N(5) nitrogen atom accelerates the cyclization about two times., the same substitution at N(3) accelerates about 50x, whereas at N(1) it results in a 300 fold retardation. With the hydantoinamides having R3 = CH3, the cyclization rate of the protonated hydantoinamide increases with increasing concentration of hydrochloric acid, whereas with the other derivatives this value is independent of the acid concentration.

Structure Investigations of Agonists of the Natural Neurotransmitter Acetylcholine VI [1]. X-Ray Structure Analysis of Trimethyl[2-(propionyloxy)ethyl]- ammonium-iodide (O-Propionylcholine-iodide)

1986 ◽  
Vol 41 (5-6) ◽  
pp. 641-646 ◽  
Author(s):  
Alfred Gieren ◽  
Michail Kokkinidis
Keyword(s):  
Crystal Structure ◽  
Nitrogen Atom ◽  
Formula Unit ◽  
Ammonium Iodide ◽  
Asymmetric Unit ◽  
Torsion Angles ◽  
Methyl Group ◽  
X Ray ◽  
Acetylcholine Chloride ◽  
Structure Investigations

The title compound (1) crystallizes in the orthorhombic, noncentrosymmetric space group Pna21 with a = 10.241(11), b = 12.903(12), c = 9.312(9) Å and with one formula unit per asymmetric unit. The stereochemically comparable torsion angles of the cation of 1 and of acetylcholine chloride are analogous. In the crystal structure the trimethylammonio methyl group is surrounded by three anions in the first coordination sphere. The geometry of a triangle formed by one of these counterions which occupies a special face of the N+C4 tetrahedron of the (CH3)3N+-CH2-R moiety, the nitrogen atom of the ammonium group and the oxygen atom of the carbonyl group is typical for nicotinic agonists.

Visible Light Photocatalytic Degradation of Methylene Blue over N-Doped TiO2

2014 ◽  
Vol 609-610 ◽  
pp. 141-146 ◽  
Author(s):  
Yu Long Hu ◽  
Li Qing Zhou ◽  
Hong Fang Liu ◽  
Xing Peng Guo
Keyword(s):  
Methylene Blue ◽  
Nitrogen Atom ◽  
Visible Light ◽  
Photocatalytic Degradation ◽  
Functional Group ◽  
Degradation Process ◽  
Degradation Pathway ◽  
Methyl Group ◽  
Intermediate Products ◽  
Visible Light Photocatalytic

The visible light photocatalytic degradation of methylene blue (MB) over N-doped TiO2 (N-TiO2) was investigated. The intermediate products of MB in the photocatalytic degradation process were analyzed by HPLC-MS technique. The results show that the cleavages of CS+=C and CN=C functional group in the central aromatic ring and the cleavage of N-C bond between the methyl group and nitrogen atom all can occur in the visible light photocatalytic degradation process over N-TiO2, but MB is difficult to be mineralized completely to the inorganic products. A detailed degradation pathway of MB has been proposed on the basis of a careful identification of intermediate products.

The microwave spectrum of (Z)-Ethanimine

1980 ◽  
Vol 33 (1) ◽  
pp. 1 ◽  
Author(s):  
RD Brown ◽  
PD Godfry ◽  
DA Winkler
Keyword(s):  
Dipole Moment ◽  
Nitrogen Atom ◽  
Stark Effect ◽  
Microwave Spectrum ◽  
Coupling Constants ◽  
Centrifugal Distortion ◽  
Methyl Group ◽  
Quadrupole Coupling ◽  
Asymmetric Rotor ◽  
Distortion Parameters

The microwave spectrum of ethanimine, CH3CH=NH, has been measured over the range of 18-76 GHz. A series of lines have been attributed to the Z-isomer. These have been fitted to an asymmetric rotor with inclusion of centrifugal distortion parameters. An excited torsional state has also been assigned and the barrier to internal rotation of the methyl group has been determined. The dipole moment has been evaluated from the Stark effect as 2.42 D. The quadrupole coupling constants of the nitrogen atom have been obtained from high-resolution studies. In contrast to methanimine, we found no evidence of magnetic hyperfine interaction in the structures of the multiplets.

scholarly journals Cyclopamine analogs bearing exocyclic methylenes are highly potent and acid-stable inhibitors of hedgehog signaling

2013 ◽  
Vol 9 ◽  
pp. 2328-2335 ◽  
Author(s):  
Johann Moschner ◽  
Anna Chentsova ◽  
Nicole Eilert ◽  
Irene Rovardi ◽  
Philipp Heretsch ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Hedgehog Signaling ◽  
Potent Inhibitor ◽  
Biological Evaluation ◽  
Luciferase Expression ◽  
Acid Stability ◽  
Methyl Group ◽  
F Ring ◽  
Synthesis And Biological Evaluation ◽  
Acid Stable

The chemical synthesis and biological evaluation of new cyclopamine analogs bearing exocyclic methylenes in different positions is described. Bis-exo-cyclopamine 6 was identified as a potent inhibitor of the Gli1-dependent luciferase expression in Shh-LIGHTII cells. An extension of this study to F-ring-modified structures shows the necessity of a rigidly positioned nitrogen atom for bioactivity as well as the presence of the C21 methyl group for acid stability and bioactivity.

The alkali metal adducts of acetophenone anil

1967 ◽  
Vol 45 (15) ◽  
pp. 1785-1794 ◽  
Author(s):  
James G. Smith ◽  
C. Doreen Veach
Keyword(s):  
Nitrogen Atom ◽  
Alkali Metal ◽  
Alkyl Halide ◽  
Chemical Behavior ◽  
Methyl Group ◽  
Metal Adducts ◽  
Hydrolysis Of

Contrary to previous reports, the reaction between acetophenone anil and sodium produces a product containing one atom of sodium per mole of anil. In its chemical behavior, this adduct appears to consist of equal parts of N-sodio-N,1-diphenylethylamine and α-sodioacetophenone anil. Thus, treatment with an alkyl halide results in products derived by alkylation of the nitrogen atom of N,1-diphenylethylamine and alkylation of the methyl group of acetophenone anil.The behavior of acetophenone anil towards lithium is quite different and very solvent dependent. In ether, hydrolysis of the lithium adduct produces a dimer, N,N′,2,3-tetraphenyl-2,3-butanediamine. In tetrahydrofuran with either lithium or potassium, another dimer, N,N′,l,4-tetraphenyl-1,4-butanediamine, is formed by dimerization through the methyl group of acetophenone anil. The structure of this new dimer was established by separation of the diastereomers and cyclization of each to the corresponding 1,2,5-triphenylpyrrolidine.The mechanism by which these products are formed is discussed.

Sigma and Pi Electron Contributions to Long-range Spin–Spin Coupling Constants in the Methyl Derivatives of the Fluoropyridines

1972 ◽  
Vol 50 (14) ◽  
pp. 2344-2350 ◽  
Author(s):  
J. B. Rowbotham ◽  
T. Schaefer
Keyword(s):  
Nitrogen Atom ◽  
Long Range ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Coupling Mechanism ◽  
Methyl Group ◽  
Spin Coupling Constants ◽  
Methyl Derivatives ◽  
Spin Spin Coupling ◽  
Derivatives Of

Seven methyl derivatives of the 3- and 4-fluoropyridines are synthesized and their p.m.r. spectra are analyzed. The nuclear spin–spin coupling constants are compared with previous results for the four methyl derivatives of 2-fluoropyridine. A model in which the nitrogen atom polarizes primarily the σ electron system of the ring, leaving the π electron contribution to the coupling mechanism relatively unaffected, qualitatively accounts for the large majority of the coupling constants. For example, the coupling over six bonds between methyl protons and a fluorine nucleus, [Formula: see text] is the same whether the fluorine atom or the methyl group is placed ortho to the nitrogen atom and is little different from its value in p-fluorotoluene. The model is consistent with significant σ electron contributions to long-range couplings over four and five bonds from methyl protons to fluorine nuclei or ring protons. Evidence is adduced for resonance structures in which fluorine conjugates with nitrogen or with ring carbon atoms. An earlier suggestion, that hyperconjugation of the methyl group with nitrogen is necessary to the interpretation of the observed couplings, is dropped. Instead, a substantial polarization of the σ electron core near C-2 and -6 is invoked but apparently does not extend appreciably beyond these atoms in the ring.

Sign in / Sign up

Export Citation Format

Share Document