3-aryl-5-arylamino

Although 3-amino-l,2,4-thiadiazoles (e.g. the 5-phenyl homolog) fail to yield nitrosamines under the usual conditions,126 5-nitrosamines are well known.81, 5,190,191 Thus, 3-alkoxy-,8 3-alkylthio-,85 3-dialkyl-amino-,87 and 3-alkylsulfonyl-5-amino-86 (243) as well as 3-aryl-5-arylamino-l,2,4-thiadiazoles,74 on treatment with the calculated quantity of sodium nitrite in dilute mineral acid, or concentrated formic acid, yield crystalline nitrosamines (244). Their unusual stability has permitted a close study of their formation and properties. 170 Their positive Liebermann reaction85,87,170 and the results of their methylation (outlined in the reaction scheme) show that nitro-sation occurs in the side-chain and not in the nucleus.170... 

Arylamino)quinoline-3-carboxylates (693) were prepared by the cyclization of /V -aryl(arylamino)methylenemalonamates (252) on the action of phosphoryl chloride in boiling benzene or of phosphorus pentoxide in refluxing xylene (46JA1246). Phosphoryl chloride proved to be a more effective cyclization agent than phosphorus pentoxide. This method could not be applied for the preparation of 4-alkylaminoquinoline-5-carbox-ylates. 

Benzothiazole, 2-amino-6-thiocyanato-azo dyes from, 1, 328 Benzothiazole, 2-aryl-synthesis, 6, 321 Benzothiazole, 2-arylamino-synthesis, 6, 323 Benzothiazole, 2-aryloxy-Fries rearrangement, 6, 289 Benzothiazole, 2-benzyl-picrate, 6, 252 Benzothiazole, 2-chloro-dyes from, 1, 321-322 synthesis, 6, 323 Benzothiazole, 2,3-dihydro-oxidation, 6, 272 Benzothiazole, 2-dimethylamino-synthesis, 5, 128... 

Furoxans, aroylamino-synthesis, 6, 414 Furoxans, aryl-reactions, 6, 412 Furoxans, arylamino-synthesis, 6, 414 Furoxans, arylaminobutyl-synthesis, 6, 423... 

Imidazolidin-2-one, l-(5-nitro-2-thiazolyl)-pharmacological activity, 6, 328 Imidazolidin-4-one, l-aryl-3-phenyl-2-thioxo- C NM S, 355 Imidazolidinones C NMR, 5, 355 Imidazolidin-2-ones nucleophilic displacement, 5, 428 polymers, 1, 279-280 reactivity, 5, 376 synthesis, 5, 466, 471 Imidazolidin-4-ones synthesis, 5, 468 Imidazoline, 2-alkyl-synthesis, 5, 463 Imidazoline, 2-amino-applications, 5, 498 Imidazoline, 2-aryl-synthesis, 5, 463 Imidazoline, 2-methyl-synthesis, 5, 487 Imidazoline, 2-nitroamino-synthesis, 5, 471 2-Imidazoline, 2-arylamino-tautomerism, 5, 368 2-Imidazoline, 1-benzyl-methylation, 5, 425 2-Imidazoline, 1,2-diaryl-synthesis, 5, 463... 

Theophylline, 9-aryl-synthesis, 5, 576 Theophylline, 8-arylamino-synthesis, 5, 576 Theophylline, 9-benzyl-rearrangement, 5, 534 Theophylline, 8-chloro-reduction, 5, 541 Theophylline, 6-deoxy-reduction, 5, 541 Theophylline, 8-dimethylamino-synthesis, 5, 580 Theophylline, 8-methyl-synthesis, 5, 591 Theophylline, 8-methylthio-synthesis, 5, 578 Theophylline, 8-nitro-synthesis, 5, 538 Theophylline, 7-phenyl-synthesis, 5, 581 Theophylline, 8-phenyl-7-oxide... 

Thiazoline, trans-2-amino-4,5-dimethyl-synthesis, 6, 310 2-Thiazoline, 2-aryl-synthesis, 6, 307, 308, 309 2-Thiazoline, 2-arylamino-tautomerism, 6, 248 2-Thiazoline, 2-dialkylamino-synthesis, 6, 308 2-liiiazoline, 5-imino-synthesis, 5, 461 2-"niiazoline, 2-mercapto-hydrolysis, 6, 272 oxidation, 6, 272 synthesis, 6, 307 2-Thiazoline, 2-methyl-aldehyde synthesis from, 1, 469 2-Thiazoline, 2-methyl-acetylation, 6, 270 acylation, 6, 270 H NMR, 6, 243... 

Thiophene, 2-amino-3-cyano-5-phenyl-synthesis, 4, 888-889 Thiophene, 3-amino-4,5-dihydro-cycloaddition reactions, 4, 848 Thiophene, 2-amino-3-ethoxycarbonyl-ring opening, 4, 73 Thiophene, 2-amino-5-methyl-synthesis, 4, 73 Thiophene, 2-anilino-synthesis, 4, 923-924 Thiophene, aryl-synthesis, 4, 836, 914-916 Thiophene, 2-(arylamino)-3-nitro-synthesis, 4, 892 Thiophene, azido-nitrenes, 4, 818-820 reactions, 4, 818-820 thermal fragmentation, 4, 819-820 Thiophene, 3-azido-4-formyl-reactions... 

The synthesis of 5-aminothiazoles via the reaction of isocyanate derivatives with aminomalononitrile p-toluenesulfonate (AMNT) has been investigated. It was found that AMNT 12 reacted with alkyl and aryl isothiocyanates in l-methyl-2-pyrrolidine (NMP) to furnish 5-amino-2-(alkylamino)-4-cyanothiazoles (13a) and 5-amino-2-(arylamino)-4-cyanothiazoles (13b-c) in 44-81 % yields. " ... 

Taber and Tian have employed the Neber protocol to prepare a-aryl azirines that underwent thermal rearrangement to afford substituted indoles via a unique Ie type ring closure <06JACS1058>. A variety of substituted N-alkyl and N-aryl indoles have been prepared by Zhao and co-workers who observed Ie cyclization of 2-aryl-3-arylamino-2-... 

More recently, the El and electrospray ionization (ESI) mass spectra of 2,5-diaryl- and 2-arylamino-5-aryl-l,3,4-oxadiazoles, as well as their complexes with copper cations, were studied. Under ESI conditions, loss of NH3 and HNCO, from complexes of 2,5-diphenyl-l,3,4-oxadiazole, 2,5-bis(2-pyridyl)-l,3,4-oxadiazole, or 2,5-bis(4-pyridyl)-1,3,4-oxadiazole with copper cation, was observed <2004JMP272>. An unusual elimination of isocyanic acid was found in fragmentation of some protonated 2,5-diaryl derivatives <2002RCM390>. 

V,iV -Diarylguanidino)-3,5-bis(methylthio)[l,2,4]triazoles 60 undergo base-induced cyclization to give 7-aryl-6-arylamino-3-methylthio-77/-[l,2,4]triazolo[4,3-7][l,2,4]triazoles 61 (Equation 10) <1988H(27)161>. Similarly, the cyclization of the iV-substituted 4-ureido and 4-thioureido derivatives of 3-phenyl-4,5-di hydro-1//-[ 1,2,4] triazole-5-thiones 62 affords 7-substituted. 5//-[l,2,4]triazolo[4,3- ][l,2,4]triazol-6(7//)-one and -triazole-6(7//)-thiones 63, respectively (Equation 11) <1991RRC619>. 

In the case of 4-(./V,./V -diaryl)guanidines 64, base-induced cyclization occurs at carbon bearing the methylthio to give the corresponding 7-aryl-6-arylamino-2-methyl-777-[l,2,4]triazolo[4,3- ][l,2,4]triazol-3(2//)-thiones 65 (Equation 12) <1986H(24)3363,1987JP(1)2667>. 

Dibromo-l,4-xylene or its 2,5-dichloro derivative is obtained by bromination or, correspondingly, chlorination of 1,4-xylene. It is oxidized to form 2,5-dibro-moterephthalic acid or its dichloro derivative 59. Subsequent reaction with aryl-amine, for instance in the presence of copper acetate, affords 2,5-diarylamino-terephthalic acid 60. It is also possible to replace the halogen atoms stepwise by arylamino moieties [11]. Cyclization to form linear trans-quinacridones, as in the above-mentioned method, is achieved by using acidic condensation agents ... 

Dimethyl (arylamino)cyanomethylenemalonates (349) were prepared in 27-52% yields in the reactions of aryl isothiocyanates and potassium cyanide in methanol at room temperature for 45 min, followed by treatment with dimethyl chloromalonate for 3 hr (77S607). 

A similar intramolecular cyclization of 3-arylamino-2-chloropropanonitriles under basic conditions to yield l-aryl-2-cyanoaziridines (Scheme 5.2) also proceeds more smoothly when benzyltriethylammonium chloride is added to the reaction mixture [20], The procedure is not suitable, however, for the preparation of /V-alkyl analogues. 

The kinetics of reactions between aroylpyruvic acids, ArC0CH2C0C02H, and arylamines in toluene show evidence of several mechanistic features intramolecular carboxyl catalysis, and catalysis by a second molecule of nucleophile, either on its own, or in concert with an (external) carboxylic acid. An extended solvent study shows an increase in the efficiency of the aforementioned intramolecular carboxyl catalysis with decreasing polarity of the solvent.Hydrolysis of the related /3-keto esters, methyl 4-aryl-2-arylamino-4-oxobut-2-enoates [ArC0CH=C(NHAr)C02Me] in aqueous dioxane is subject to general acid catalysis. " ... 

Very early in the history of heteroeyelic chemistry it was diseovered by Dimroth (09LA183) that l-aryl-5-amino-l,2,3-triazole (1, R = H) undergoes a faeile, reversible isomerization to 5-(arylamino)-l,2,3-triazole (2, R = H) (Scheme IV.4). 

A mixture of alkyl azides, substituted phenyl isothiocyanate and aryl or alkyl isocyanate are reported to yield 5-arylamino-l,2,4-thiadiazolin-3-ones (283) via a proposed 1,2,3,4-thiatriazoline (282) (Scheme 64) <84CHEC-I(6)463>. 

---