Reaction Of Aromatic Amines Research Articles

Diastereoselective three-component Mannich reaction catalyzed by silica-supported ferric hydrogensulfate

A highly anti-diastereoselective three-component Mannich reaction of aromatic amines and aromatic aldehydes with cyclohexanone in the presence of silica-supported ferric hydrogensulfate has been developed. The best selectivity was obtained where there were electron-donating groups on both aldehyde and amine. Selectivity decreases when electron-withdrawing groups are present on the aldehyde; in these cases selectivity is improved if an electron-donating group is present on the amine.

Synthesis of N-Substituted Pyrroles Under Catalyst- and Solvent-Free Conditions

N-Substituted pyrroles were synthesized under neat conditions by the reaction of aromatic amines with 2, 5-dimethoxytetrahydrofuran in excellent yields.

Tracing of ethyl 2-acetyl-3-(arylamino)butanoate intermediates (β-amino ketones) and their structural confinement

Tracing of ethyl 2-acetyl-3-(phenylamino)butanoate intermediates (β-amino ketones) was performed during the course of N-arylpiperidone synthesis by reaction of aromatic amines, acetaldehyde, and ethyl acetoacetate. The structural confinement and stereochemistry of these molecules were explained by use of 2D NMR spectroscopy and X-ray crystallography.

Diporphyrinylamines: Synthesis and Electrochemistry

The synthesis of three possible diporphyrinylamines is described. All compounds were obtained by using the Buchwald-Hartwig aromatic amination reaction. The electronic spectra of the three porphyrin dimers showed characteristic features found in highly delocalized systems. The first oxidation of these compounds took place on the connecting amine function.

Research on some Schiff Base Compounds with Aromatic Substituted Groups and their Cu-Complexes

Some Schiff base compounds with aromatic substituted groups and their Cu-complexes have been designed and synthesized from the reaction of aromatic amines with salicylaldehyde. It has been found that depending on the molecular structures and substituted groups, the formed Schiff base compounds showed different properties, indicating distinct regulation of molecular design. UV and IR data confirmed commonly the formation of Schiff base and coordination with Cu(II) ions, as well as aromatic segment in molecular structures. In addition, the process of ex situ coordination seemed to change differently along with adding time, which could be ascribable to the presence of distinct substituted group and change of reaction activity. The spectral difference is mainly attributed to molecular structures, formation of Schiff base group and different substituted groups. The present results have showed that the special properties of Schiff base compounds could be turned by modifying molecular structures and substituted groups, which show potential application in fields of functional material fields such as liquid crystal and catalysts.

ChemInform Abstract: Total Syntheses of Nitrogen‐Containing Cyclic Natural Products Based on Aryl Amination

AbstractReview: ca. 50 refs.

Synthesis of Schiff bases by aromatic amine condensation with 3,3′-bithiophenes-2,2′ and 4,4′-dicarbaldehydes

Reactions of aromatic amines with 3,3′-bithiophene-2,2′-dicarbaldehyde 1 and 3,3′-bithiophene-4,4′-dicarbaldehyde 2 gave the 2,2′-(N-(aryl)diimino)-3,3′-bithiophene 3 and 4,4′-(N-(aryl)diimino)-3,3′-bithiophene 4 in good yields. Orthophenylenediamine reacted with 1 and 2 to give dithieno[3,4-c;4′,3′-e]azepino[1,2-a]benzimidazole 5 and dithieno[2,3-c;3′,2′-e]azepino[1,2-a]benzimidazole 6. All these original products have been characterized by spectroscopic techniques and elemental analysis.

Novel and efficient aqueous phase synthesis of N-substituted azepines via tandem Michael addition and cyclization in the presence of β-cyclodextrin

N-substituted azepines were synthesized for the first time in water under neutral conditions by the reaction of aromatic amines, dimethyl/diethyl acetylene dicarboxylate, 2,5-dimethoxytetrahydrofuran mediated by β-cyclodextrin in high yields. β-Cyclodextrin can be recovered and reused with just a small loss of catalytic activity.

Functionalized Ionic Liquid Promoted Aza‐Michael Addition of Aromatic Amines

AbstractA functionalized ionic liquid, 3‐(N,N‐dimethyldodecylammonium) propanesulfonic acid hydrogen sulphate ([DDPA][HSO4]) has been used as catalyst for the aza‐Michael reactions of aromatic amines with α,β‐unsaturated compounds at room temperature to produce β‐amino compounds in good yields. The catalyst can be reused for several times without obvious loss of the catalytic activity.

ChemInform Abstract: Synthesis of Tetrahydroquinolines from Aromatic Amines, Formaldehyde, and Electron Rich Alkenes: Evidence for Nonconcertedness.

Abstract The one pot synthesis of Tetrahydroquinolines can be achieved by reaction of aromatic amines and formaldehyde with a variety of electron rich alkenes including styrenes and enol ethers. The cyclisation is multi-step as evidenced by the isolation of intermediates, which can be cyclised to give the @Tetrahydroquinolines, and by the observation of side-products such as oxazines, and in the case of o-phenylenediamine, the interesting tricycle (4)

ChemInform Abstract: Direct Substitution of Aromatic Ethers by Lithium Amides. A New Aromatic Amination Reaction.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A facile synthesis of novel unsymmetrical N-(4-oxo-2-phenyl-3(4 H)-quinazolinoyl)- N-(aryl)acetamidines

A series of novel unsymmetrical N-(4-oxo-2-phenyl-3(4 H)-quinazolinoyl)- N-(aryl)acetamidines was synthesized by reacting ethyl(1 E)- N-(4-oxo-2-phenylquinazolin-3(4 H)-yl)ethanimidoate ( 2) and suitable reactive aromatic amines. Structures’ determination of the synthesized compounds was carried out using spectroscopic techniques including IR, 1H NMR, and mass spectrometry. Structural effects on reactivity were also studied.

Two isolated intermediates of the Tröger's base: synthesis and mechanism

By controlling the amount of catalyst 1-methyl-3-(2-(sulfooxy)ethyl)-1 H-imidazol-3-ium chloride, two new intermediates of Tröger's bases ( 11, 1,6-dimethyl-3-(4-methylphenyl)-1,4-dihydroquinazolin-3-ium tetrafluoroborate and 12, 8-methyl-2,5-bis-(4-methylphenyl)-3,5,6,7-tetrahydropyrimido[5,6,1- ij]quinazoline-2-ium tetrafluoroborate) were simply obtained from the one-pot reaction of aromatic amine and formaldehyde in ionic liquid at ambient temperature. These results support the mechanism for Tröger's base formation supposed by Fernando Coelho and co-workers. However, the crystal structure of 12 and correlative quantum chemistry calculation results are not reconciled with their report.

芳香族アミノ化反応を基盤とする含窒素環状天然物の全合成

This article focuses on the development of an aromatic amination reaction using CuI and CsOAc and its application to total syntheses of nitrogen-containing cyclic natural products. The reaction conditions present several unprecedented features that have not been observed in conventional palladium-catalyzed systems, including high functional group compatibility (e.g., N-alloc-and sp2-Br are retained) and applicability for highly hindered substrates. The utility of this reaction has been fully demonstrated through total syntheses of duocarmycins, yatakemycin, and PDE-II.

Supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinolines

Natural supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinoline derivatives by the reaction of aromatic amine and cyclic enol ether in excellent yield with high diastereoselectivity has been developed. Carbohydrates, cellulose, and starch were converted into their sulfonic acid derivative and these scaffolds exhibit efficient catalytic properties, along with excellent cost effectivity and recyclability.

Palladium-Catalyzed Conjugate Addition to Give Aspartic Acid Derivatives

In related work, the groups of Hii and Sodeoka have reported asymmetric addition reactions of aromatic amines to α,β-unsaturated carbonyl compounds such as N-alkenoyl oxazolidinones or N-alkenoyl carbamates catalyzed by cationic BINAP-palladium complexes (Adv. Synth. Catal. 2006, 348, 587; Org. Lett. 2004, 6, 1861). In the present study, the authors utilize dicationic palladium complex 1 in conjugate addition reactions of aromatic amines to fumaryl pyrrolidinone to afford after hydrolysis aspartic acid derivatives in very good yields and enantiomeric ratios.

Na-Y Zeolite as a Highly Active Catalyst for the Hydroamination of α,β-Unsaturated Compounds with Aromatic Amines

Hydroamination of α,β-unsaturated compounds with less reactive aromatic amines was investigated over Na-Y zeolite. Aniline gave the 99% conversion at 100 °C for 5 h over Na-Y zeolite, resulting in the formation of N-[2-(methoxycarbonyl)ethyl]aniline with excellent mono-selectivity. However, aromatic amines having an electron-withdrawing functional group gave moderate conversions. The reactions using recovered catalyst also occurred without significant decrease in the catalytic activity during four recycles. The regeneration of used Na-Y zeolite can be performed by the calcination. Solid-state 13C MAS NMR measurement revealed that methyl acrylate was effectively activated by Na-Y zeolite.

Heavier Group‐2‐Element Catalyzed Hydroamination of Carbodiimides

The heteroleptic calcium amide [{ArNC(Me)CHC(Me)NAr}Ca{N(SiMe3)2}(THF)] (Ar = 2,6‐diisopropylphenyl) and the homoleptic heavier alkaline earth amides, [M{N(SiMe3)2}2(THF)2] (M = Ca, Sr and Ba) are reported as competent pre‐catalysts for the hydroamination of 1,3‐carbodiimides. Whilst the reaction scope is currently limited to reactions of aromatic amines with 1,3‐dialkylcarbodiimides, in most cases preparations in hydrocarbon solvents proceed rapidly at room temperature with catalyst loadings as low as 0.2 mol‐% and the guanidine reaction products crystallize directly from the reaction mixture. Initial studies are consistent with the intermediacy of heavier group‐2 guanidinate complexes.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Sulfonic Acid Functionalized Silica: An Efficient Heterogeneous Catalyst for a Three-Component Synthesis of 1,4-Dihydropyridines under Solvent-Free Conditions

Sulfonic acid functionalized silica catalyzed the three-component reaction of aromatic amines, alpha,beta-unsaturated aldehydes and beta-keto esters forming the corresponding 1,4-dihydropyridines in short reaction times and in high yields.

Synthesis of β-amino carbonyl compounds via a Mannich reaction catalyzed by SalenZn complex

Abstract A practical method was developed to synthesize a series of new β-amino carbonyl compounds via a three-component Mannich reaction of aromatic amines with aromatic aldehydes and active methylene compounds catalyzed by SalenZn complex under mild reaction condition. The catalyst and solvent effects were investigated. The substituted group effects of aromatic amines and aldehydes were also discussed.