2-Anilino-l-hydroxy

D° [Amin Oxiran 1 1] Zeolith ZCP-50/ Benzol, Ruckfl. 9 h [Amin Oxiran — 1 1] Zn-(2 J ,3 R)-tartrat/ CH2C12, 20-25% 7d 1 Anilino-2-hydroxy-octan + 2-Anilino-l-hydroxy-octan (-7 3) (1 R,2R)-2-Anilino-l-hydroxy-cyclohexan (ee 52 %) 90 28 3 4... 

Ar — CH = N — OH + R2B-CH2-CH = CH-CH3) Cyclopentan 2-Anilino-l-hydroxy-E16d, 1124 (Addition/Hydro-lyse)... 

Anilino-l-hydroxy- E16d, 1125/ 1209 (Oxiran + Amin) 2-Hydroxy-l-[(2-... 

Anilino-4-hydroxy-5-phenyI-l,3-thiazol (R = OH R2 = R3 = CSHS R4 = H)515 Eine Mischung von l,5g (0.078 mol) 2-Amino-4-hydroxy-5-phenyl-l,3-thiazol, 0,73 g (0,078 mol) Anilin und 15 m/ Eisessig wird 2 h unter RiickfluB erhitzt. Nach Zugabe von heiBem Wasser und Abkuhlen scheidet sich das farblose Produkt ab es wird abgesaugt und aus Ethanol umkristallisiert Ausbeute 1,4 g (72%) Schmp. 191-191,5°. 

Hydroxy-5-(4-hydroxy-2-phenyl-4,5-dihydro-1,3-thiazol-4-yl)-2-phenyl- 356 4-Hydroxy-2-[4-(l-hydroxy-2,2,2-trifluor-l-trifluormethyl-ethyl)-N-methyl-anilino]- 127 4-Hydroxy-5-(3-indolyl-methyl)-2-mercapto- 100 4-Hydroxy-2-isopropylamino-5-phenyl-... 

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]. 

Benzylische Acyloxy-Gruppen wie z.B. in 4,7-Diacetoxy-6-methoxy-2-methyl-l,2,3,4-te-trahydro-isochinolin werden bei der Reaktion mit primaren Aminen unter milden Bedin-gungen durch eine Alkylamino- Oder Arylamino-Gruppe ersetzt gleichzeitig wird die zwei-te Acetoxy-Gruppe im Molekul hydrolysiert, so daB man mit Ethylamin bzw. Anilin 4-Ethylamino-7-hydroxy-6-methoxy-2-methyl- (82%) bzw. 4-Anilino-7-hydroxy-6-meth-oxy-2-methyl-l,2,3,4-tetrahydro-isochinolin (66%) erhalt1. 

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. 

QfN"CH3 + HO- Y0 20% 48 h 3-Hydroxy-2-hydrOXymethyl-l-methyl-4-( N-methyl-anilino)-1,2,3,4- tetrahydro-chinolin 45 7... 

By this method, sulfur dyes derived from 4-hydroxydiphenylamine are seen to be essentially identical. Similarly, the sulfur dye from 7-anilino-9-methyl-l,2,4-trichlorophenothiazin-3-one (21) and the sulfur dye from 4-anilino-4 -hydroxy-2-methyldiphenylamine (22) were compared and found to be almost identical, as was the related trichlorophenothiazinone derivative (23) from carbazole when compared with Hydron Blue indophenol, Cl... 

Anilino-3-hydroxy-l,2,4-thiadiazole dissolves in dilute alkalis and is reprecipitated by dilute acid it is, however, appreciably soluble in more concentrated acids (e.g. 3A-hydrochloric acid), possibly due to the influence of the basic portion of the heterocylic nucleus.130... 

III,D, 1). In spite of this, differences in the spectra of 5-anilino-3-hydroxy- and 3-alkoxy-5-anilino-l,2,4-thiadiazoles suggest that ketonic tautomers of the hydroxy compound contribute to the resultant absorption curve. Similar observations are made with 3-hydroxy-5-phenyl-l,2,4-thiadiazole.122 The spectra of 4-methylpyrimid-2-one and 2-methoxy-4-methylpyrimidine led to similar conclusions.170... 

Acylation of 3-hydroxy-l,2,4-thiadiazoles (184) by the usual procedures yields monosubstitution products that are formulated as phenolic esters (e.g. 185 R = Ph R = Ac, Bz, or p-MeC6H4S02)178 (see also ref. 130). 5-Anilino-3-hydroxy-1,2,4-thiadiazole affords diacetyl and dibenzoyl derivatives one acyl residue being assumed to enter the hydroxyl group, the possible structures of the derivatives are 186a-c.130... 

Benzotriazine (20) shows the following IR bands vmax(KBr) = 1473, 1383, 877, 800 and 750 cm-1 (75JCS(Pl)3l). In the IR spectra of l,2,3-benzotriazin-4-ones an intense band between 1700 and 1667 cm-1 is observed, showing that the hydroxy tautomer (lOd) can be excluded. Similarly, it was shown that in l,2,3-benzotriazine-4-thiones (22) the thione form predominates in the solid state. The IR spectra of 4-anilino-l,2,3-benzotriazines (23) show a strong absorption band at 1145 10 cm-1 which is absent in the 3-aryl-4-imino isomers (24) and presents a useful means of distinction between these isomers (70JCS(C)765). 

With the l,3,5-triazin-2-yl derivatives of 4,4 -diaminostilbene-2,2 -disulfonic acid proposed by B. Wendt in 1940 [25], optical brighteners came into full-scale industrial use. In 1941, 4,4 -bis (4-anilino-6-hydroxy-l,3,5-triazin-2-yl)aminoJstil-bene-2,2 -disulfonic acid disodium salt was introduced commercially under the trade name Blankophor B (3) [1264-32-0],... 

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). 

Hydroximino-l-(4-methyl-phenyl)-E14b, 313 (aus En-on) fram-l-tN-Methyl-anilinojA-oxo-E16d, 794 (Anilinierung) Cyclopenten n.s-5-Anilino-3-hydroxy- Vl/la, 1, 461 Cyclopent[b indol 8b-Hydroxy-l,2,3,3a,4,8b-hexahydro- E6b/1, 577 (2-Br —anilin + R-CO-CI/... 

Azetidin l-Anilino-4,4-dimethyl-3-(l-hydroxy-ethyl)-2-oxo- E16b, 545 (aus cycl. Carbonsaure-hydrazid)... 

Anilinotrimethylolmethane N-(Trimethylol-me thane)-aniline P henylaminotrimethylol-methane N-Phenyl-(tris-hydxoxymethyl)-methylamine 2-Anili no- 2- hydroxy me thyl-1,3-dihydroxypropane 2-Anilino-2-hydroxy-. methyl-l,3-propanediol or Phenyltrimethylol-methylamine, CjHi. NH.C(CHjOH)3. This may be considered as the parent compd of the derivs described below ... 

Hydroxy-l -pheny Ipyrazolo- Raney Ni 2-Anilino-3-carbamoyl 458... 

Hydroxy-2-(4-methyl-anilino)-l, 3-thiazol-l-oxid 37% Schmp. > 360°... 

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