Proton-mediated practical synthesis of McGeachin-type bisaminals

Synthesis ◽  
2021 ◽  
Author(s):  
Yang Chen ◽  
Tingting Wang ◽  
Hongguang Du ◽  
Jiaxi Xu ◽  
Zhanhui Yang
Keyword(s):  
Proton Donor ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Synthetic Method ◽  
Substituted Anilines ◽  
Fluoroacetic Acid ◽  
Practical Synthesis

A proton-mediated practical synthesis of McGeachin-type bisaminals from 2-alkylamino arenecarbaldehydes and primary amines is achieved, with tri-fluoroacetic acid as the proton donor. The use of proton, a smallest electro-philic activator, allows previously inviable ortho-substituted anilines and linear and branched aliphatic amines to be viable substrates for McGeachin bisami-nal synthesis. Overcoming the steric and electronic limitations provides a practical synthetic method. The applications in product derivation and phar-maceutical molecule modification are also demonstrated.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

ChemInform Abstract: The “Benzostabase” Protecting Group for Primary Amines. Application to Aliphatic Amines.

ChemInform ◽  
2010 ◽  
Vol 23 (15) ◽  
pp. no-no
Author(s):  
R. P. BONAR-LAW ◽  
A. P. DAVIS ◽  
B. J. DORGAN ◽  
M. T. REETZ ◽  
A. WEHRSIG
Keyword(s):  
Aliphatic Amines ◽  
Primary Amines ◽  
Protecting Group

Molekülinterne Dipolorientierung und dielektrische Absorption in verdünnter Lösung bei Mikro- und Submillimeter-Wellen. I. Primäre Amine / Intramolecular Dipole Reorientation and Dielectric Loss of Microwaves and, Submillimetrewaves in Diluted Solution I. Primary Amines

1982 ◽  
Vol 37 (2) ◽  
pp. 102-112
Author(s):  
G. Klages ◽  
E. Wieczorek
Keyword(s):  
Dipole Moment ◽  
Dielectric Loss ◽  
High Frequency ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
High Frequency Region ◽  
Debye Relaxation ◽  
Diluted Solution ◽  
Wave Region ◽  
Molecular Resonances

Abstract The dielectric loss of very diluted solutions of four aromatic and three aliphatic amines in three non polar aliphatic solvents at 20 °C has been measured. The wave numbers cover 0.1 to 200 cm-1 . It is shown, how to analyse the microwave spectra of the loss factor ε″ in terms of three absorption areas, two of Debye relaxation type and the high frequency one of Lorentz resonance type. To limit the latter at its high frequency side, the extinction coefficient a has been used to determine and separate the lowest molecular resonances. From the analysis, dispersion steps and the components of the dipole moment due to the three absorption regions are calculated. Comparison with the so called optical dispersion step insures within the limits of experimental error that the absorption due to orientation of the permanent dipole moment is covered by the measured band. The long wave region belongs to the rotation of the molecules, the two others to intramolecular reorientation. In aromatic amines not all molecules of the sample are able to invert their NH2 group, but slower orientation by hindered inversion happens. On the other hand, in aliphatic amines the group is rotating and the high frequency region may be due to Foley absorption.

scholarly journals One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

2019 ◽  
Vol 15 ◽  
pp. 2840-2846
Author(s):  
Valeriya G Melekhina ◽  
Andrey N Komogortsev ◽  
Boris V Lichitsky ◽  
Vitaly S Mityanov ◽  
Artem N Fakhrutdinov ◽  
...  
Keyword(s):  
Starting Material ◽  
Primary Amines ◽  
Synthetic Method ◽  
One Pot ◽  
One Pot Synthesis ◽  
Major Reaction Product ◽  
Major Reaction

The condensation of primary amines with N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamides was explored. Thus, a previously unknown recyclization of the starting material was observed in acidic ethanol in the presence of an amine, which provided the corresponding dihydropyrrolone derivative as the major reaction product. Based on this transformation, a practical and convenient one-pot synthetic method for substituted pyrrolo[3,4-b]pyridin-5-ones could be devised.

Visible light promoted deaminative difluoroalkylation of aliphatic amines with difluoroenoxysilanes

2020 ◽  
Vol 56 (91) ◽  
pp. 14247-14250
Author(s):  
Yang Huang ◽  
Jia Jia ◽  
Qi-Ping Huang ◽  
Liang Zhao ◽  
Pan Wang ◽  
...  
Keyword(s):  
Visible Light ◽  
Aliphatic Amines ◽  
Primary Amines

A visible light promoted deaminative strategy for the difluoroalkylation reaction utilizing pyridinium-activated aliphatic primary amines and difluoroenoxysilane as substrates has been developed.

Practical Synthesis of Urea Derivatives from Primary Amines, Carbon Monoxide, Sulfur, and Oxygen under Mild Conditions.

ChemInform ◽  
2007 ◽  
Vol 38 (1) ◽  
Author(s):  
Takumi Mizuno ◽  
Masatoshi Mihara ◽  
Toshiyuki Iwai ◽  
Takatoshi Ito ◽  
Yoshio Ishino
Keyword(s):  
Carbon Monoxide ◽  
Primary Amines ◽  
Urea Derivatives ◽  
Mild Conditions ◽  
Practical Synthesis

The gaseous oxidation of tertiary aliphatic amines II. Trimethylamine

1958 ◽  
Vol 246 (1244) ◽  
pp. 91-98 ◽  
Keyword(s):  
Carbon Monoxide ◽  
Nitrogen Oxides ◽  
Major Part ◽  
Aliphatic Amines ◽  
Inert Gas ◽  
Primary Amines ◽  
Present System ◽  
Peroxy Radicals ◽  
Heterogeneous Process ◽  
Powerful Effect

A study of the slow oxidation of trimethylamine shows that the reaction has no autocatalytic character and rapidly becomes inhibited as the products accumulate, eventually ceasing completely while the major part of the initial reactants remains unchanged. Both the rate and extent of oxidation are reduced by increased surface but additions of an inert gas have no influence on the reaction. The main stable products are formaldehyde and dimethylamine together with smaller amounts of nitrogen and carbon monoxide; neither methylamine nor ammonia nor nitrogen oxides can be detected at any stage of reaction. Separate experiments on the influence of additives show that dimethylamine, although it acts as an inhibitor, does not exert a sufficiently powerful effect to account for the observed results, and it is clear that some other compound with more pronounced inhibiting properties must also be formed in small quantities. It is suggested that NN -dimethylhydroxylamine, which is an exceptionally powerful inhibitor, may be formed either by oxidation of (CH 3 ) 2 N. radicals or by some heterogeneous process. The absence in the present system of primary amines, which are among the principal products of triethylamine oxidation, may be due to the fact that for steric reasons intramolecular attack of intermediate peroxy-radicals derived from trimethylamine cannot take place.

scholarly journals Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8–DMSO: application to the synthesis of vernakalant

2015 ◽  
Vol 11 ◽  
pp. 1008-1016 ◽  
Author(s):  
Dnyaneshwar N Garad ◽  
Subhash D Tanpure ◽  
Santosh B Mhaske
Keyword(s):  
Dimethyl Sulfoxide ◽  
Ammonium Persulfate ◽  
Primary Amines ◽  
Radical Mechanism ◽  
Forming Process ◽  
One Pot ◽  
Practical Synthesis ◽  
Cyclic Imides ◽  
Cyclic Anhydrides ◽  
High Yields

Ammonium persulfate–dimethyl sulfoxide (APS–DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.

Practical Synthesis of a PCP-Type Pincer Ligand and Its Metal Complexes­

Synthesis ◽  
2017 ◽  
Vol 50 (05) ◽  
pp. 1015-1019 ◽  
Author(s):  
Kazutaka Matoba ◽  
Yoshiaki Nishibayashi ◽  
Aya Eizawa ◽  
Shunsuke Nishimura ◽  
Kazuya Arashiba ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Transition Metal ◽  
Metal Complexes ◽  
Transition Metal Complexes ◽  
Large Scale ◽  
Crystal Structure Analysis ◽  
Synthetic Method ◽  
Pincer Ligand ◽  
X Ray ◽  
Practical Synthesis

A synthetic method for N-heterocyclic carbene- and phosphine-based PCP-type pincer ligand is described on a large scale. Some transition-metal complexes bearing the PCP-type pincer ligand are prepared and characterized by X-ray crystal structure analysis.

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