5-Anilino-2- 2- -ethyl

Anilino-ethyl)-5-phenyl-... 2- (3-Anilino-propyl)-5-phenyl-... 5- ( Imino-pyrrolidino-methyl)-amino -3-phenyl-... 

Verwcndet man in der 3. Stufe des angegebenen Formelschemas einen Aldehyd anstelle des Alkyl-bromids, so erhalt man einen jS-Amino-alkohol, z. B. durch Metallierung von (2-Anilino-ethyl)-quecksilber-bromid (aus Ethen durch Aminomercurierung) mit Phenyllithium und anschlicBende Umsetzung mit 2-Methyl-propanal l-Anilino-3-hydroxy-4-methyl-pentan (70%)2. 

The only example of this system has been reported in a patent (83EGP156815). 5-Amino-l-benzoyl/substituted benzoyl-4-ethoxycarbo-nylpyrazolyl-3-thiones (72) react with either ethyl 3-anilino or substituted anilinocrotonates in boiling ethanol in the presence of metallic sodium to give 2-(a-anilino/substituted anilino)ethyl-5-benzoyl/substituted ben-... 

ETHYL P-ANILINOCROTONATE (Crotonic acid, P-anilino-, ethyl ester)... 

Aoetyloxy)ethyl)phenylamino)propanenitrile N-Acetoxyethyl-N-cyanoethylaniline Aniline, N-acetoxy-ethyl-N-cyanoethyl- 2-(N-(2-Cyanoethyl)anilino)ethyl acetate EINECS 244-7404 Propanenitrile,... 

COUMARILIC ACID, 24, 33 Coumarin, 24, 33 Coumarin dibromide, 24, 33 Coumarin, 4-methyl-, 24, 69 Coupling, of allyl chloride, 27, 7 of aryl residues, 20, 45 Crab shells, 26, 36 Creatinine, 22, 90 /i-Cresol, 2-bromo-, 23,11 Crotonaldehyde, 24, 92 27, 66 Crotonic acid, SO, 101 24, 98 26, 55 Crotonio acid, /3-anilino-, ethyl ESTER, 29, 42 Cupric acetate, 28, 45 Cupric carbonate, basic, 24, 64 Cupro-cupri sulfite, 28, 53 Cuprous bromide, 24, 22, 23 Cuprous chloride, 28, 46 Cuprous cyanide, 21, 89 24, 14, 97 28, 34... 

However, when the nucleophilicity of the nitrogen, at a fixed position in the haloamine, is reduced, the intramolecular 3, 2 process (13) is supplemented by another closely related one. For example -anilino-ethyl bromide (11) loses a proton from the NH group, and the resulting anion undergoes cyclization (reaction 14) For amines of still lower... 

Most of the antagonists of the direct effects belong to the same series of piperazine derivatives (Godfraind) lidoflazine (l-[4,4-di-(4-fluorophenyl)-butyl -4-2, [6-dimethyl-anilinocarbonyl-methyl]-piperazine) and R7427 (l-[4,4-di-(4-fluoro-phenyl)-butyl]-4-[2-(N-ethyl-anilino)-ethyl]-piperazine trihydrochloride). 

Another category Ic indole synthesis involves cyclization of a-anilino aldehydes or ketones under the influence of protonic or Lewis acids. This corresponds to retro.synthetic path d in Scheme 4.1. Considerable work on such reactions was done in the early 1960s by Julia and co-workers. The most successful examples involved alkylation of anilines with y-haloacetoacetic esters or amides. For example, heating IV-substituted anilines with ethyl 4-bromoacetoacetate followed by cyclization w ith ZnClj gave indole-3-acetate esterfi]. Additional examples are given in Table 4.3. 

Ethyl 3-anilinocrotonate (82) undergoes reaction with dimethyl acetylene-dicarboxylate (57) with the formation of two products, ethyl 5-anilino-3,4-dicarbomethoxy-trfl s,cM-2,4-hexadienoate (83) and ethyl 5-anilino-3,4-dicarbomethoxy-ci5, cw-2,4-hexadienoate (84). 

Dichloro-l,3,5-triazanaphthalene and its 6-methyl derivative react at the 4-position (70-90% yields) with ammonia in dioxane (20°, 15 min) or in water (95°, 1.5 hr) and with diethylamine in dioxane (20°, 15 min). The dichloroazine yields the 4-(A-ethyl-anilino)-2-chloro derivative under acidic conditions. Amination of the 2,4-dithioxo derivative with concentrated ammonia (95°,... 

Treating 2 -ani lino-6 -[/V-ethyl-/V-(3-methoxypropyl)ami no]-3 -methyl-fluoran (88) with 48% hydrobromic acid in the presence of concentrated sulfuric acid at 110-11 5 °C gives 2 -anilino-6 -[/V-(3 -bromopropyl)-7V-ethylamino]-3 -methylfluoran (89)70 in excellent yield (Eq. 10). 

Preparation of 2 -Anilino-6 - [N- (3-bromopropyl) -N-ethylaminoJ-3 -methylfluoran (89). To a mixture of 2 -anilino-6 -[/V-ethyl-Af-( 3-methoxy-propyl)amino]-3 -methylfluoran (0.1 mol) and 48% hydrobromic acid (150 ml) was added dropwise concentrated sulfuric acid (20 ml) with vigorous stirring. Then, the resulting mixture was stirred at 110-115 °C for 1 h, poured into ice water (1000ml), and made alkaline by aqueous sodium hydroxide. The pale violet precipitate was filtered off, and recrystallized from ethyl acetate-isopropanol to give 2 -anilino-6 -[/V-(3-bromopropyl)-,V-ethylamino]-3 -methylfluoran in 96% yield, mp 160-162 °C. 

Preparation of 2 -Anilino-6 - N-ethyl-N-[3-(4-methylthiophenoxy)pro-pyl]amino -3 -methylfluoran (90a). A mixture of 2 -anilino-6 -[7V-(3-bro-... 

Anilino-2-quinoxalinecarbaldehyde (183, R = Ph) and diethyl malonate (184) gave ethyl 2-oxo-l -phenyl-1,2-dihydropyrido[2,3-/ quinoxaline-3-carboxy-late (185, R = Ph) (trace piperidine, trace AcOH, PhH, reflux with H20 removal, 4 h 55% analogs likewise).143... 

Perhaps the earliest reported method for the synthesis of the 1,2,3-thiadiazole ring system was the one described by Pechmann and Nold in which diazomethane was reacted with phenyl isothiocyanate. Of the four possible isomers that could be obtained from the reaction, 5-anilino-l,2,3-thiadiazole 62 (R1 Ph, R2 = H) was the only product formed (Equation 16) <1896CB2588>. This method continues to be used as a route to 5-amino substituted 1,2,3-thiadiazoles. 4,5-Disubstituted 1,2,3-thiadiazoles have been produced in excellent yield by reaction of l,l -thiocar-bonyl diimidazole with ethyl diazoacetate <1988SUL155>. 

Fig. 10.1 Structures ofthe fluorescent whitening agents included in this study. Full names DAS 1,4,4 -bis[4-anilino-6-morpholino-1,3,5-triazin-2-yl)-amino]stilbene-2,2 -disulphonate DSBP, 4,4 -bis(2-sulfostyryl)biphenyl BLS, 4,4 -bis(4-chloro-3-sulfostyryl)biphenyl. Internal standard 4,4 -bis-5-ethyl-3-sulfobenzofur-2-yl)biphenyl.

Ethyl 2-ethylthio-4-chloro-5-pyrimidinecarboxylate (XXIIa), as well as the corresponding4-hydroxy-(XXIIb) and 4-amino-(XXIIIa) derivatives, possess-anti-cytogenic activity on Neurospora crassa [223, 224]. Compounds (XXIIIa, b and c) were found to inhibit the conversion of orotic acid to the uridine nucleotides [202]. Ethyl 2-methylthio-4-(halo-substituted anilino)-5-pyrimidinecarboxylates (XXIV), particularly the o-bromo- and the o-chloro- derivatives, substantially inhibit the growth of five experimental mouse tumours (Krebs-2 ascites carcinoma, Ehrlich carcinoma clone 2, leukaemia L-1210, carcinoma 755 and lymphocytic neoplasm P-288) [225]. Compounds of this type are usually prepared by the base catalysed condensation of ethoxymethylenemalonic esters or related derivatives with urea, thiourea, guanidine, or substituted amidine-type analogues [212, 225-237]. 

Amino-anilino)-l, 2-diphenyl-cyclopropenylium-tetrafluoroborat [mesomer mit (2-Amino-phenyl)-(l,2-diphenyl-cyclopropenyliden)-ammonium-tetrafluoroborat] cyclisiert beim Ver-such der Deprotonierung mit molaren Mengen an Diisopropyl-ethyl-amin (Hunig-Base) unter Ringspaltung zu 2-[(Z)-l,2-Diphenyl-ethenyl -benzimidazol (89% Schmp. 273-2740)59 (vgl. 

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