2-Aryl-3-arylazo

Aryl-arylazo-sulfane reagieren mit 2-Hydroxy-naphthalin in alkalischem Ethanol zu Azo-Verbindungen. Die Reaktionen werden dutch elektronenliefernde Substituenten im N-Aryl-Teil erleichtert bzw. im S-Aryl-Teil erschwert1. 

Coumarin, 7-amino-7-(diethylamino)-, I, 333 Coumarin, 7-amino-4-methyl-fluorescence spectra, 3, 601 Coumarin, 7-amino-3-phenyl-brightening agents, I, 339 Coumarin, 4-aryl-occurrence, 3, 677 synthesis, 3, 810 Coumarin, 3-arylazo-4-hydroxy-structure, 3, 643 Coumarin, 3-bromo-reactions... 

Jap-KIingermarm reactions, 4, 301 oxidation, 4, 299 reactions, 4, 299 synthesis, 4, 362 tautomerism, 4, 38, 200 Indole, 5-amino-synthesis, 4, 341 Indole, C-amino-oxidation, 4, 299 tautomerism, 4, 298 Indole, 3-(2-aminobutyl)-as antidepressant, 4, 371 Indole, (2-aminoethyl)-synthesis, 4, 278 Indole, 3-(2-aminoethyl)-synthesis, 4, 337 Indole, aminomethyl-reactions, 4, 71 Indole, 4-aminomethyl-synthesis, 4, 150 Indole, (aminovinyl)-synthesis, 4, 286 Indole, 1-aroyl-oxidation, 4, 57 oxidative dimerization catalysis by Pd(II) salts, 4, 252 Indole, 1-aroyloxy-rearrangement, 4, 244 Indole, 2-aryl-nitration, 4, 211 nitrosation, 4, 210 synthesis, 4, 324 Indole, 3-(arylazo)-rearrangement, 4, 301 Indole, 3-(arylthio)-synthesis, 4, 368 Indole, 3-azophenyl-nitration, 4, 49 Indole, 1-benzenesulfonyl-by lithiation, 4, 238 Indole, 1-benzoyl photosensitized reactions with methyl acrylate, 4, 268 Indole, 3-benzoyl-l,2-dimethyl-reactions... 

Pyrimidine, I-alkyl-2-methyltetrahydro-C-thioacylation, 4, 807 Pyrimidine, 4-alkylsulfinyl-nucleophilie displaeement reaetions, 3, 97 Pyrimidine, 6-alkylsulfinyl-nucleophilic displacement reactions, 3, 97 Pyrimidine, 2-alkylsulfonyl-nueleophilie displaeement reactions, 3, 97 Pyrimidine, 4-alkylsulfonyl-nucleophilic displacement reactions, 3, 97 Pyrimidine, 6-alkylsulfonyl-nucleophilie displaeement reactions, 3, 97 Pyrimidine, alkylthio-dealkylation, 3, 95 desulfurization, 3, 95 oxidation, 3, 96 synthesis, 3, 135, 136 Pyrimidine, 2-alkylthio-aminolysis, 3, 96 hydrolysis, 3, 95 Prineipal Synthesis, 3, 136 Pyrimidine, 4-alkylthio-aminolysis, 3, 96 hydrolysis, 3, 95 Pyrimidine, 6-alkylthio-aminolysis, 3, 96 hydrolysis, 3, 95 Pyrimidine, 4-allenyloxy-rearrangement, 3, 93 Pyrimidine, 4-allyloxy-2-phenyl-rearrangement, 3, 93 Pyrimidine, 4-allynyloxy-rearrangement, 3, 93 Pyrimidine, 4-anilino-2,5,6-trifluoro-NMR, 3, 63 Pyrimidine, 2-aryl-pyrroleaeetic aeid from, 4, 152 Pyrimidine, arylazo-synthesis, 3, 131 Pyrimidine, 4-arylazo-reduetion, 3, 88... 

Thiazolin-5-one, 2-alkoxy-4-arylazo-rearrangements, 5, 777 2-Thiazolin-5-one, 4-methyl-2-phenyl-protomeric equilibrium, 6, 249 4-Thiazolin-2-one, 4-aryl-reactions, 6, 286 4-Thiazolin-2-one, 3,4-dimethyl-protonation, 6, 286 4-Thiazolin-2-one, 4-methyl-reactions, 6, 286 Thiazolinones electrophilic attack, 5, 99 Thiazolin-2-ones IR spectroscopy, 6, 241 nucleophilic displacement, 5, 100 2-Thiazolin-4-ones reactions, 6, 287 2-substituted synthesis, 6, 306 synthesis, 5, 129 6, 309, 310 tautomerism, 6, 248 2-Thiazolin-5-ones IR spectroscopy, 6, 242 reactions, 6, 288 synthesis, 5, 138 tautomerism, 6, 249 4-Thiazolin-2-ones synthesis, 6, 314 4-Thiazolin-3-ylacetic acid esters... 

Oxidation of 5-arylazo-6-aminoquinoline 146 with copper sulfate in pyridine gave the corresponding 2-aryltriazolo[4,5-/]quinolines 147. Condensation of halo-genated nitrobenzenes with triazolo[4,5-/]quinoline 145 yielded the appropriate 2H- and 3//-aryl derivatives. The nitration of 3-phenyl-3//-triazolo[4,5-/]quino-line 147 occurred at position 4 of the phenyl ring (Scheme 46) (73T221). 

Arylazo-de-sulfonation 319 Arylazophenylsulfones, azo-extrusion 211 l-Aryl-2-benzenesulfonhydrazides, axo-extru-sion 211 Aryl cations... 

Sulfones are thermally very stable compounds, diaryl derivatives being more stable than alkyl aryl sulfones which, in turn, are more stable than dialkyl sulfones allyl and benzyl substituents facilitate the homolysis by lowering the C—S bond dissociation energy17. Arylazo aryl sulfones, on heating in neutral or weakly basic media at 100°C, yield an aryl and arenesulfonyl radical pair via a reversible one-bond fission followed by dediazoni-ation of the aryldiazenyl radical (see Scheme 2 below)20. However, photolysis provides a relatively easy method for generating sulfonyl radicals from compounds containing the S02 moiety. 

It was shown that furoxans can be transformed to 1,2,3-triazoles. Thus, 4-acetylamino-3-arylazo-l,2,5-oxadiazole 2-oxides undergo two successive (cascade) mononuclear heterocyclic rearrangements in an aqueous basic medium with the formation of 4-acetylamino-2-aryl-5-nitro-2/7-l,2,3-triazoles (Equation 12) <2001MC230>, or 3,3 -disubsti-tuted 4,4 -azo-l,2,5-oxadiazole 2-oxides were found to undergo a rearrangement into 2-(furoxan-4-yl)-4-nitro-2//-1,2,3-triazole 1-oxides on heating in pertrifluoroacetic or peracetic acids (Equation 13) <2003MC272>. 

Arylazo-4-(3-ethoxycarbonylureido)furoxans 62, which were synthesized by the reactions of 4-amino-3-arylazo-furoxans with ethoxycarbonyl isocyanate, were subjected to cascade rearrangements under the action of potassium r/-butoxidc in dimethylformamide or by heating in dimethyl sulfoxide to form 4-amino-2-aryl-5-nitro-2//-l,2,3-triazoles 63 (Scheme 13) <2001MC230, 2003RCB1829>. 

Diazonujm Salts as Electrophu.es. 2-Aryl-5(47/)-oxazolones 225 couple readily with aryldiazonium salts to give the corresponding 4-arylazo derivatives 226 or 2-aryl-4,5-oxazoledione-4-arylhydrazones Structural studies revealed that... 

Tab.6 5-Arylazo-pyrimidine aus Pyrimidinen mit Aryl-diazonium-Salzen... 

Aryl-4-arylazo-2-hydroxy-l, 3-thiazole werden durch Kupplung aromatischer Diazonium-Salze mit N-Thiobenzoyl-glycinen erhalten1 ... 

Aryl-3-arylazo- in 60-75% Ausbeute. Mit 5-Amino-... 

Oxalsaure-bis-nitrilimine, die aus den entsprechenden Oxalsaure-bis-[2-aryl-hydrazonid]-dichloriden in situ freigesetzt werden, dimerisieren in geringer Ausbeute zu 5-Aryl-3,6-bis-[arylazo]-1 -dehydro-[Pg.86]

Tab.9 Aryl-hetaryl-azo-Verbindungen aus Arylazo-Verbindungen durch Aufbau des Hetaren-Systems... 

Die Reaktion verlauft genauso erfolgreich fur Arylazo-hydroxy-naphthaline und -pyra-zole. Wie aus den Reaktionszeiten ersichtlich ist, verlauft die Reaktion leichter, wenn eiektronenziehende Substituenten den Aryl-Rest aktivieren. 

Bis-[aryl-hydrazono]-cyclodecaneiibergefuhrt. Durch Oxidationdieser Hydrazone mit Blei(IV)-acetat werden 9,10-Bis-[arylazo]-dekaline I sowie l,6-Bis-[arylazo]-l,6-diacetoxy-cyclodecane II in unterschiedlichen Ausbeuten gebildet. Zur Oxidation werden die Hydrazone bei 20° in Dichlormethan zwei Stunden mit Blei(IV)-acetat behandelt2 ... 

Die a,/J-ungesattigte Carbonyl-Verbindung 2-Methyl-4-oxo-2-penten bildet mit Aryldiazo-nium-Salzen in Anwesenheit von Titan(III)-Salzen als Reduktionsmittel in doppelter Re-aktion unter Stickstoff-Verlust 3-Aryl-2-arylazo-2-methyl-4-oxo-pentane. AuBer Titan(III)-Salzen konnen auch andere Reduktionsmittel verwendet werden3 ... 

Dimethylfuran-3(2ff)-one undergoes coupling with arenediazonium salts at pH 0 and furnishes 2-arylazo-2,5-dimethylfuran-3(2//)-ones which are readily converted into 1 -aryl-5-methyl-3-pyrazolones (79S283). 

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