- Non-reductive conversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinones
-
Heating 1-nitro-9,10-anthraquinone 2 with ureas 4 in N,N,N',N'-tetramethylurea (TMU) at around 130 °C resulted in the displacement of the nitro group by the amino groups, leading to the corresponding aminoanthraquinones 5 in good yields.
- Suzuki,Kawakami,Maeda
-
-
Read Online
- Solvent-free, microwave assisted oxidation of alcohols with 4-hydroxypyridinium chlorochromate functionalized silica gel
-
4-Hydroxypyridinium chlorochromate functionalized silica gel was found to be an efficient and reusable oxidant for the very fast oxidation of primary and secondary alcohols to the corresponding carbonyl compounds under solventfree conditions and microwave irradiation in excellent yields.
- AHMADI, Sayed Ali,GHALEHBANDI, Shermineh Sadat,GHAZANFARI, Dadkhoda,SHEIKHHOSSEINI, Enayatollah
-
p. 283 - 289
(2020/10/06)
-
- A triazine-phosphite polymeric ligand bearing cage-like P,N-ligation sites: An efficient ligand in the nickel-catalyzed amination of aryl chlorides and phenols
-
A novel P,N-ligand was introduced for efficient Ni-catalyzed amination of aryl chlorides. Reaction of cyanuric acid (1,3,5-triazine-2,4,6-triol) and trichlorophosphine (PCl3) resulted in the production of a new porous material (TPPM) containing triazine rings with phosphite moieties in a sheet morphology. Cavities in the prepared compound create sites on the surface of the material with appropriate ligation character to coordinate with metals for catalytic purposes. The nickel-catalyzed amination of aryl chlorides and of phenols in their 2,4,6-triaryloxy-1,3,5-triazine (TAT) protected form were efficiently accomplished in the presence of this easily prepared and reusable P,N-ligand under mild reaction conditions. More importantly, TPPM was reusable for 5 iterations following this protocol without significantly decreasing in its activity.
- Panahi, Farhad,Roozbin, Fatemeh,Rahimi, Sajjad,Moayyed, Mohammadesmaeil,Valaei, Aria,Iranpoor, Nasser
-
supporting information
p. 80670 - 80678
(2016/10/12)
-
- DEVICE FOR DETECTING AN ANALYTE
-
Devices for detecting an analyte comprising a redox active analyte sensitive material on a working electrode and computer assisted signal acquisition and processing.
- -
-
-
- Carbon-carbon cleavage of aryl diamines and quinone formation using sodium periodate: a novel application
-
A first novel synthetic utility of sodium periodate for aryl diamine carbon-carbon cleavage is described. Aryl 1,2-diamine compounds were successfully converted into corresponding nitriles, while the developed method is also useful for the preparation of quinones from corresponding aryl 1,4-diamine compounds. The advantages of this protocol are shorter reaction time and mild reaction conditions to obtain moderate to good yields.
- Telvekar, Vikas N.,Takale, Balaram S.
-
experimental part
p. 3940 - 3943
(2010/08/07)
-
- A novel application of (Diacetoxyiodo)benzene for carbon-carbon cleavage of aryl diamines and synthesis of quinones
-
A novel synthetic utility of hypervalent iodine reagent, (diacetoxyiodo)benzene for diamino aryl carbon-carbon cleavage is described. 1,2-Diamino aryl compounds were successfully converted into the corresponding nitriles, while the developed method was also useful for the preparation of quinones from corresponding 1,4-diamino aryl compounds. The advantages of this protocol are shorter reaction times and mild reaction conditions to obtain moderate to good yields.
- Telvekar, Vikas N.,Bachhav, Harshal M.
-
experimental part
p. 2059 - 2062
(2010/10/19)
-
- Chemoselective reduction of azides with sodium sulfide hydrate under solvent free conditions
-
Sodium sulfide hydrate has been employed for an efficient reduction of a variety of azides to the primary amines in good-to-excellent yields under solvent-free system and without perturbing many active functionalities such as ether, carbonyl, sulfonyl, and nitro.
- Kazemi, Foad,Kiasat, Ali Reza,Sayyahi, Sohyl
-
p. 1813 - 1817
(2007/10/03)
-
- Synthesis of 2,6-Dihydronaphthindol-6-ones
-
The reaction of 1-aminoanthraquinone with benzyl chloride in KOH-DMSO system afforded 3,11b-dibenzyl-2-phenyl-2,3,7,11b-tetrahydroanthraoxazin-7-one (5; 78percent yield), whose structure was determined by single-crystal X-ray diffraction.The reaction of compound 5 with aluminium chloride gave 1-phenyl-2,6-dihydronaphthindol-6-one (52percent yield) having strong fluorescence.
- Arai, Sadao,Yamauchi, Sigeaki,Yamagishi, Takamichi,Hida, Mitsuhiko
-
p. 324 - 326
(2007/10/02)
-
- Substituent Effects in Anthrasemiquinones
-
Electron spin resonance spectra have been obtained from series of 2-substituted anthrasemiquinones and of 3-substituted 1,8-dihydroxyanthrasemiquinones.The proton splittings are consistently assigned by means of linear correlation plots between splitting constants and a substituent-dependent paramater.All lines in the plots of he two series of compounds obey the following linear equation aRi = AixR + aHi where aHi and aRi are the splitting constants at position i before and after the substituent has been added.Ai is the slope of the line for the splittings from position i and xR is a constant characteristic of the substituent R. xR is comparable to the Hammett ? parameter.Electron-donating substituents at C-2 are shown to increase the spin densities at the positions 1 > 6 > 8, and to decrease them at the positions 4 > 3 > 7 > 5, with the strength of the effect indicated.Electron-withdrawing substituents have the opposite effect.Preliminary Hueckel molecular-orbital calculations qualitatively predict the observed correlations, solely by changing the parameter for the resonance integral.
- Pedersen, Jens A.
-
p. 3223 - 3232
(2007/10/02)
-
- PHOTOCHEMICAL DECOMPOSITION OF 2-AZIDOPHENAZINE IN ALCOHOLS AND IN THE PRESENCE OF CYANIDE ION
-
The photochemical decomposition of 2-azidophenazine in alcoholic solvents has been investigated. 1-Amino-2-alkoxyphenazines are formed in neutral and (in higher yield and together with 2-amino-1-chlorophenazine) in acidic conditions, while the azepinoquinoxaline 7 is formed in basic conditions.With cyanide ion nucleophilic attack takes place giving 1-amino-2-phenazine carbonitrile.To allow comparison, 2-azidonaphthalene, 2-azidoanthracene and 2-azidoanthraquinone have also been photodecomposed in the conditions in which the most interesting results are obtained from 2-azidophenazine.The mechanism of these reactions is briefly discussed.
- Albini, Angelo,Bettinetti, Gian Franco,Fasani, Elisa,Pietra, Silvio
-
-
- PHOTOCHEMICAL HYDROXYLATION OF ANTHRAQUINONE IN SULFURIC ACID
-
The photolysis of anthraquinone in sulfuric acid leads to hydroxylation of its ring with the preferential formation of 2-hydroxyanthraquinone in concentrated and 1-hydroxyanthraquinone in dilute sulfuric acid.The second hydroxy group only enters photochemically at position 4 of 1-hydroxyanthraquinone if the latter is activated by complex formation with boric acid.During photolysis in deaerated sulfuric acid the nitroanthraquinones are reduced photochemically to (hydroxyamino)anthraquinones; here 1-(hydroxyamino)anthraquinones with an unoccupied para position in the same condensed benzene ring undergo rearrangement under the reaction conditions to 1-amino-4-hydroxyanthraquinones.The main photochemical stage of hydroxylation in concentrated sulfuric acid is nucleophilic substitution of hydrogen in the monoprotonated anthraquinone by the HSO4(-) ion, while in dilute sulfuric acid it is electron transfer from water to anthraquinone.
- Studzinskii, O.P.,El'tsov, A.V.
-
p. 1666 - 1673
(2007/10/02)
-
- ARYLATION OF 2-AMINOANTHRAQUINONES BY HALOGENOBENZENES
-
2-Amino-, 1-chloro-2-amino-, and 2-amino-3-chloroanthraquinones react with halogenobenzenes in nitrobenzene in the presence of an acid-combining agent and copper catalyst to form initially 2-phenylaminoanthraquinones, which are then converted into 2-(diphenylamino)anthraquinones.In the reaction of 1-chloro-2-aminoanthraquinone with halogenobenzenes, in addition to mono- and diarylation of the amino group dehalogenation of the anthraquinone ring occurs both in the initial compound and in the arylation products, and N,N'-diphenylindanthrene is also formed.
- Krasnosel'skaya, M. I.,Gudzenko, V. I.
-
p. 717 - 720
(2007/10/02)
-
- PHOTOCHEMICAL REACTION OF 9,10-ANTHRAQUINONE AND ITS DERIVATIVES WITH PYRIDINE
-
The previously unknown photochemical reaction of 9,10-anthraquinone with pyridine in an atmosphere of argon takes place with formation of 2-(1,2-dihydropyridino)- or 2-(1,4-dihydropyridino)-9,10-anthraquinone, which is converted by the action of alkali into 2-aminoanthraquinone.In the presence of atmospheric oxygen the reaction product after treatment whith alkali is 1-aminoanthraquinone in addition to 2-aminoanthraquinone.The 1- and 2-methoxyanthraquinones and chloroanthraquinones react with pyridine in the light and form, after treatment with alkali, substituted aminoanthraquinones.
- Loskutov, V.A.,Lukonina, S.M.,Konstantinova, A.V.,Fokin, E.P.
-
p. 500 - 504
(2007/10/02)
-
- Reactions of 1,5-Dichloroanthrachinone with Nucleophiles
-
Reactions of 1,5-dichloroanthraquinone (1) with various nucleophiles were examined to evaluate possibilities for selective substitution. 1-Amino-5-chloroanthraquinone was obtained from 1 by reaction with (a) sodium azide in dimethyl sulfoxide and (b ammonia in the presence of potassium fluoride, but 1 with potassium in ammonia gave 3-chlorobenzoic acid.Conditions were found for preferential substitution in reactions of 1 with (c) 4-toluidine, (d) hexamethylphosphoric triamide, and (e) N-methylformamide.Reagent e is preferred for making 1-chloro-5-(methylamino)anthraquinone, though this compound predominates in mixtures produced when d is used.Potassium hydroxide in 2-ethoxyethanol converts 1 to the corresponding mono- and diethers of 1,5-dihydroxyanthraquinone, while sodium hydrosulfide and 1 give bis(5-chloroanthraquinonyl)sulfide.
- Ruediger, Edward H.,Kaldas, Magdy L.,Ghandi. Sham S.,Fedryna, Cristi,Gibson, Martin S.
-
p. 1974 - 1978
(2007/10/02)
-
- Chemistry of Quinones. Part 6. The Selective Hydrolysis of α-Acetoxyanthraquinones and Related Compounds by Trifluoroacetic Acid Containing Small Amounts of Water
-
Acetoxy- or benzoyloxy-substituents adjacent to the carbonyl groups of anthraquinone, 1,4-naphthoquinone, naphthacene-5,12-quinone, benzophenone, and methyl benzoate are selectively converted into hydroxy-groups by treatment with trifluoroacetic acid containing small amounts of water.In the absence of water a reversible acidolysis occurs.Water reacts with the acylating agent, thus preventing the reverse reaction.Evidence is presented that the hydrolyses are of the AAC1 type.
- Harrison, Charles R.,Hodge, Philip,Khan, Naeem
-
p. 1592 - 1594
(2007/10/02)
-
- Process for preparing aminoanthraquinones
-
A process for preparing aminoanthraquinones of high purity, which comprises catalytically hydrogenating nitroanthraquinones in the suspended state in an aqueous medium in the presence of a hydrogenating catalyst. In a preferred embodiment, the catalytic hydrogenation may be carried out in the presence of an organic or inorganic base, followed, if desired, by oxidizing the hydrogenation product.
- -
-
-
- Azo pigments derived from 2-hydroxy-3-carboxynaphthalene containing a substituted or unsubstituted phthalimide
-
Azo pigments derived from 2-hydroxy-3-carboxy-naphthalene and containing a substituted or unsubstituted phthalimide radical. The majority give red colorations and due to their excellent fastness properties are particularly valuable for use in surface coatings and resins.
- -
-
-
