5-Arylamino-2-phenyl

Gomaa MS, Lim AS, Lau SC, Watts AM, Illingworth NA, Bridgens CE, Veal GJ, Redfern CP, Brancale A, Armstrong JL, Simons C (2012) Synthesis and CYP26A1 inhibitory activity of novel methyl 3-[4-(arylamino)phenyl]-3-(azole)-2,2-di-methylpropanoates. Bioorg Med Chem 20 6080-6088... 

Anilino-4-arylthiazoles (211) are mercurated on the phenyl ring (Scheme 133) (453. 454). The phenyl ring is also the site of mercuration in 2-arylamino-4-(2-thienyl)thiazoles (213) (Scheme 134) (455). 

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... 

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... 

Treatment of 4-arylamino-8-iodoquinoline 268 with propargyl alcohol in presence of iodo(phenyl)bis(triphenylphosphine) palladium and copper (I)iodide afforded 269 which upon catalytic reduction using Linder s catalyst gave 4//-pyrrolo[3,2,l-(/]quinoline 270 (97H2395) (Scheme 48). 

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>. 

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>. 

The formation of substituted quinolines 35 (58-90% yield) by intramolecular cyclization of 4-arylamino-l-azabutadienes 2 has been carried out at 100°C using one equivalent of aluminium chloride the reaction involves the diene moiety and one carbon—carbon double bond of the aromatic ring (87S82). The participation of the phenyl group attached to the a-... 

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... 

The products of the thermolysis of 3-phenyl-5-(arylamino)-l,2,4-oxadiazoles and thiazoles have been accounted for by a radical mechanism.266 Flash vacuum pyrolysis of 1,3-dithiolane-1-oxides has led to thiocarbonyl compounds, but the transformation is not general.267 hi an ongoing study of silacyclobutane pyrolysis, CASSF(4,4), MR-CI and CASSCF(4,4)+MP2 calculations using the 3-21G and 6-31G basis sets have modelled the reaction between silenes and ethylene, suggesting a cyclic transition state from which silacyclobutane or a trcins-biradical are formed.268 An AMI study of the thermolysis of 1,3,3-trinitroazacyclobutane and its derivatives has identified gem-dinitro C—N bond homolysis as the initial reaction.269 Similar AMI analysis has determined the activation energy of die formation of NCh from methyl nitrate.270 Thermal decomposition of nitromethane in a shock tube (1050-1400 K, 0.2-40 atm) was studied spectrophotometrically, allowing determination of rate constants.271... 

Details of the Diels-Alder addition of aromatic nitroso-compounds to thebaine to give adducts (117), the ring-opening of these to 14-hydroxylamino-compounds (118 R = OH), the reduction of these to 14-arylamino-compounds (118 R = H), and cyclization to (119) have been published.162 Dihydro-thebaine-< 4-phenyl ether (120 R = OPh) has been transformed into the benzylisoquinoline (121) by potassamide in liquid ammonia, but the same transformation could not be effected with the free phenol (120 R = H) or with the deoxy-compound (120 R = H).163... 

Arylamino- -2-oxid E2, 640 2-(Bis-[2-ehlor-ethyl]-amino)- -2-oxid E2, 515 2-(Bis-[2-chlor-ethyl]-amino)- -2-sulfid XII/2, 777 2-Chlor-3,4-dimethyl-5-phenyl- -2-sulfid E2, 677 2-Chlor- -2-oxid... 

Reactions of 1,2,4-thiadiazoles with radicals and electron deficient species are virtually unknown. Catalytic and dissolving metal reductions usually result in S—N bond cleavage. For example, the 5-anilino-3-hydroxy derivative (51) gives a good yield of l-phenyl-2-thiobiuret (52) on Zn-HCl reduction (Scheme 27). Reduction of the diamino derivative (53) gives amidinothiourea (54) from which it may be prepared by oxidation (Scheme 28). Under similar conditions, cleavage of the 3,5-diphenyl derivative (55) results in loss of sulfur and formation of benzylbenzamidine (56 Scheme 29). Reduction of 5-alkylamino-or 5-arylamino-3-alkylthio derivatives (57) with H2S in pyridine-triethylamine or sodium in liquid ammonia yields 1-substituted dithiobiurets (58 Scheme 30). 

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