Rhodium(II)-Catalyzed Synthesis ofN-Aryl-N′-tosyldiazenes from Primary Aromatic Amines Using (Tosylimino)aryliodinane: A Potent Stable Surrogate for Diazonium Salts

2017 ◽  
Vol 2017 (9) ◽  
pp. 1272-1276 ◽  
Author(s):  
Motoki Ito ◽  
Arisa Tanaka ◽  
Kazuhiro Higuchi ◽  
Shigeo Sugiyama
Keyword(s):  
Aromatic Amines ◽  
Diazonium Salts ◽  
Primary Aromatic Amines

scholarly journals Mechanisms and products of azo coupling in histochemical protease procedures based on primary aromatic amines as unspecific moieties.

1990 ◽  
Vol 38 (9) ◽  
pp. 1295-1300 ◽  
Author(s):  
H G Frank
Keyword(s):  
Azo Dyes ◽  
Aromatic Amines ◽  
Elevated Temperatures ◽  
Test Tube ◽  
Aromatic Nucleus ◽  
Diazonium Salts ◽  
Amino Group ◽  
Tissue Sections ◽  
Primary Aromatic Amines ◽  
Methylated Amines

It is presumed that the azo dyes generated by histochemical protease reactions are formed by substitution of a reactive aromatic carbon. They are referred to as dyes of the C-azo series. To confirm this assumption, the absorption spectra between 330 and 630 nm of azo dyes resulting from coupling between various aromatic amines of the aniline and naphthylamine series and the diazonium salts Fast Blue B and Fast Garnet GBC were studied in test tube experiments. Some of the amines were blocked by methylation to prevent coupling either at the amino group (N-methylated) or at the aromatic nucleus (C-methylated). Coupling was performed in buffered aqueous solutions of the diazonium salts. For analysis the azo dyes were dissolved in dimethylformamide. For acid rearrangement these solutions were acidified and incubated at elevated temperatures. After detection of dipeptidyl peptidase IV in tissue sections using Gly-Pro-4-methoxy-2-naphthylamine as substrate, the resulting dye was extracted and compared with the test tube compounds. All aromatic amines yielded azo dyes. Dyes extracted from sections and those test tube compounds derived from unmethylated or C-methylated amines showed almost identical spectral maxima, whereas dyes formed by N-methylated amines yielded different spectra. Acid rearrangement did not influence the spectral maxima of the N-methylated amine-derived dyes. Dyes resulting from C-methylated amines were destroyed. The results indicate that under histochemical conditions diazonium salts react primarily with the liberated free amino group but not with the aromatic nucleus of the unspecific moiety. Therefore, it is proposed that the formula of the final reaction product in naphthylamine-based protease histochemistry should be given as an N-azo dye, e.g., as a triazene.

Condensation of 2-Acetyl-1,3-indandione with Amines and Diazonium Salts

1979 ◽  
Vol 34 (6) ◽  
pp. 867-870 ◽  
Author(s):  
Fathy Abdel Kader Amer ◽  
El-Sayed Afsah ◽  
Hassan Etman
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Diazonium Salts ◽  
Amine Hydrochloride ◽  
Diethyl Amine ◽  
Primary Aromatic Amines ◽  
The Mannich Reaction

Abstract 2-Acetyl-1,3-indandione Derivatives, Amines, Diazonium Salts 2-Acetyl-1,3-indandione (1) undergoes the Mannich reaction with piperidine or diethyl-amine hydrochloride to give compounds 2 and 3, respectively. On treatment 1 with ethylenediamine hydrochloride and formaldehyde, 2,2′-[ethylene bis[imino(1-oxotri-methylene)]]di-1,3-indandione (4) was obtained. With primary aromatic amines it yielded 2-[N-(substituted phenyl)acetimidoyl]-1,3-indandione (5a-i). The condensation of 1 with o-aminophenol yielded a mixture of 5c and the oxazepinone (6), while condensation with 2,3-diaminopyridine gave the diazepinone (7). Mannich reaction of 5a and g with piperidine hydrochloride and formaldehyde gave 8a, b. The coupling of 1 with diazonium salts was investigated.

Catalyst- and solvent-free Csp2-H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under ball-milling

2021 ◽  
Author(s):  
Goutam Brahmachari ◽  
Indrajit Karmakar ◽  
Pintu Karmakar
Keyword(s):  
Ball Milling ◽  
Aromatic Amines ◽  
Solvent Free ◽  
One Pot ◽  
Biologically Relevant ◽  
Tert Butyl ◽  
Three Component Reaction ◽  
Primary Aromatic Amines

A one-pot procedure for the synthesis of biologically relevant coumarin-hydrazones by a three-component reaction between 4-hydrocoumarins, primary aromatic amines and tert-butyl nitrite under ball-milling in the absence of any catalyst/additive...

scholarly journals Synthesis of Organic Ligands via Reactions of 4-Benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione with N-Nucleophiles

2020 ◽  
Vol 2020 ◽  
pp. 1-9
Author(s):  
Hassan Kabirifard ◽  
Pardis Hafez Taghva ◽  
Hossein Teimouri ◽  
Niloofar Koosheshi ◽  
Parastoo Javadpour ◽  
...  
Keyword(s):  
High Temperature ◽  
Carbonyl Group ◽  
Aromatic Amines ◽  
Room Temperature ◽  
Organic Ligands ◽  
Carboxyl Group ◽  
Primary Aromatic Amines

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led to 5-phenylamino-2,5-dihydrothiophene-2-ones 6–8 as organic ligands in the medium to good yields. These showed the nucleophilic attacks of N-nucleophiles, except primary aromatic amines, on thioester carboxyl group (C-2) of thiophene-2,3-dione ring 1. However, the nucleophilic attacks of primary aromatic amines on the carbonyl group (C-3) of thiophene-2,3-dione 1 occurred in the form of substituted thiophenes.

Preparation of aromatic amines by copper-catalyzed coupling of boronic acids with aqueous ammonia

2010 ◽  
Vol 88 (9) ◽  
pp. 964-968 ◽  
Author(s):  
Zhaoqiong Jiang ◽  
Zhiqing Wu ◽  
Lixia Wang ◽  
Di Wu ◽  
Xiangge Zhou
Keyword(s):  
Aromatic Amines ◽  
Aqueous Ammonia ◽  
Environmentally Friendly ◽  
Boronic Acids ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Primary Aromatic Amines

A simple, highly efficient, and environmentally friendly protocol for the synthesis of primary aromatic amines by catalytic coupling of aromatic boronic acids with aqueous ammonia has been developed by using commercial and inexpensive CuSO4·5H2O as catalyst without addition of other solvents under mild reaction conditions.

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