Imidazole, 5-hydroxy-2- -4-phenyl

Imidazol 5-Ethoxy-t-hydroxy-2-(2-hydroxy-phenyl)-4-methyl- E8c, 52 [HO — N = C(CH3) — COOC2H5 + Ar—CH = N —OH] Malonaldehydsaure [a-(Hydroxy-methyl)-4-methoxy-benzyliden]- -amid E15/1, 682 (aus 4,5-H2-1,2-oxazol)... 

The aromatic character of the phenol ring explains the higher stability of the enol form with respect to the keto form in the ground state.Variations in the aromatic character (Induced by substitution or heteroatoms) influence the forward and reverse energy barriers for the proton transfer between the keto and enol forms. Thus, it has been found for 2-(2 -hydroxy-phenyl)imidazole (Scheme 17) that the energy dif-... 

Imidazole, 4-formyl-5-hydroxy-l-phenyl-mesoionic, 5, 372 Imidazole, 2-formyl-1-methyl-mass spectra, S, 360 Imidazole, 2-formyl-l,4,5-trimethyl-... 

Dioxo-3-alkyl-imidazolidine werden mit Lithiumalanat in der Hitze zu 3-A1-kyl-imidazolidinen reduziert z.B. 2,4-Dioxo-3-methyl-5-phenyl-imidazolidin zu 7-Methyl-4-phenyl-imidazolidin (43% d.Th.) bei 23° und inverser Zugabe wird dagegen (vgl. S. 252) 2-Hydroxy-l-methyl-4-phenyl-imidazol (66% d. Th.) erhalten, das sich unter energischen Bedingungen zum 7-Methyl-4-phenyl-imidazol (25 % d. Th.) reduzieren laftt3 ... 

US patent 6,734,308, Crystal forms of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-ethynyl-phenyl)-l-methyl-lH-quinolin-2-one, 2,3,-dihydroxy-butanedioate salts and method of production [108]. The invention relates to crystal forms of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-meth-yl]-4-(3-ethynyl-phenyl)-1 -methyl-lH-quinolin-2-one, 2,3-dihydroxy butanedioate salts, and to pharmaceutical compositions containing the above compound, methods of treating hyperproliferative diseases, such as cancers, in mammals, especially humans by administering the above compound, and to methods of preparing the crystal forms of the above compound and related compounds. 

Bis(oxazolinyl)pyridine-Ce(IV) triflate complex 78 catalyzed the enantioselective 1,3-DC of acyclic nitrones with a, 3-unsaturated 2-acyl imidazoles. For example, C-phenyl 7V-benzyl nitrone reacted with 77 in the presence of 78 to give the adduct 79 with excellent diastereo-and enantioselectivity. Isoxazolidine 79 was then converted into P -hydroxy-P-amino acid derivatives by hydrogenation of the N-0 bond in the presence of Pd(OH)2/C and cleavage of the 2-acyl imidazole with MeOTf in MeCN <06OL3351>. 

The reaction of 2-aminobenzyl alcohol 376 with 2-chloro-4,5-dihydroimidazole afforded [2-(4,5-dihydro-177-imidazol-2-ylideneamino)phenyl]methanol hydrochloride 377, which upon treatment with carbon disulfide gave l-(477-3,l-benzoxazin-2-yl)imidazolidine-2-thione 378 (Scheme 71). The assumed reaction mechanism involved the initial formation of the dithiocarbamate 379, which underwent intramolecular nucleophilic addition to furnish the unstable thiazetidine 380. By nucleophilic attack of the hydroxy group on the carbon atom of the thiazetidine ring, thiocarbamate derivative 381 was formed, which gave the final 3,1-benzoxazine 378 by an intramolecular cyclocondensation with the evolution of H2S <2006H(68)687>. 

Eine Ausnahme scheinen 5(4)-Hydroxy-4(5)-phenyl-imidazole zu bilden, die bevorzugt in der Hydroxy-Form vorliegen4. 

Bei Einsatz von z. B. 3,5-Dimethyl-l-(imino-isopropylamino-methyl)-pyrazo]/ai-Brom-aceto-phenon erhalt man infolge Hydrolyse des nicht isolierten 2-(3,5-Dimethyl-pyrazolo)-l-isopro-pyl-4-phenyl-im idazols 2-Hydroxy-1 - isopropyl-4 -phenyl- imidazol (51 %)105 ... 

Anilinocarbonyl-l-hydroxy-4-methyl-2-phenyl-imidazol-3-oxid212 ... 

Die Umlagerung von 2-Amino-5-methyl-3-(2-oxo-2-phenyl-ethyl)-1,3,4-oxadiazolium-broraid mit heiBer wiiBriger Kaliumcarbonat-Losung zu l-Acetylamino-2-hydroxy-4-phenyl-imidazol wurde bereits im Bd. X/2, S. 345 beschrieben. 

Mit Lithiumalanat werden 5-Ethoxycarbonyl-2,4-difluor-l-(methoxy-methyl)-imidazol zu 4-Fluor-4-hydroxy methyl-1-(methoxy-methyl)-imidazol499 und l-(2,6-Dimethyl-phenyl)-5-fluor-2-phenyl-4-trifluormethyl-imidazol zu l-( 2,6-Dimethyl-pheny )-2-phenyl-4-trifluormethyl-imid-azol927 reduziert. 

Hydroxy-5-methyl-4-phenyl-imidazol reduziert508. Ebenfalls mit Zink/Eisessig gelingt die Herstellung von 1-substituierten Imidazolen aus den entsprechenden 1-substituierten Imidazol-... 

Durch Singulett-Sauerstoff werden 2,4,5-trisubslituierte Imidazole mit mindestens einem Phenyl-Ring in 4(5)-Position in Ausbeuten uber 80% zu 2,4,5-trisubstituierten 2-Hydroper-oxy-2H-imidazolen oxidiert. Die Reduktion der Hydroperoxide mit Triphenylphospan fuhrt zu den entsprechenden 2,4,5-trisubstituierten 2-Hydroxy-2H-imidazolen1232 (vgl. Bd. E13, S. 562f) ... 

Die Umsetzung von 2-Acylamino-3-phenyl-propansaure-amiden mit Natrium-hypobromit verlauft iiber 2-Oxo-2,3-dihydro-imidazole, die in geringen Ausbeuten unter Ringspaltung und einer IIofmann-Rcaktion zu 2-Hydroxy-l,3,4-oxadiazolen518,556 557 reagieren ... 

A simple and direct approach to new imidazole containing ligands is the modification of commercially available imidazoles. Unfortunately, only a limited number of substituted imidazoles is available and most of them are not ideally substituted for further modification because they have only plain alkyl or phenyl substituents. An example of this approach is the synthesis of 3-aminopropylimidazole9 and 3-hydroxy-propy I imidazole10 from urocanic acid... 

Reaction of 4-aryl-7-iodoperhydropyrido]2,l-c][l,4]oxazin-6-ones (07USA2007/0117839, 08WOP2008/013213) and 7-iodo-6-oxo-4-(3,4,5-tri-fluorophenyl)perhydropyrido[2,l-a]pyrazine-2-carboxylate (07USA2007/ 0117839) with P(OEt)3 at 120 °C for 2 h afforded 7-phosphonic acid diethyl esters. 3-Hydroxy-6-arylperhydropyrido[2,l-c][l,4]oxazin-4-ones first were reacted with triphenylphosphonium bromide in refluxing MeCN, then with 3-methoxy-4-(4-methyl-lH-imidazol-l-yl)benzaldehyde at ambient temperature in the presence of NEt3 to provide (Z)-3- l-[3-methoxy-4-(4-methyl-lH-imidazol-l-yl)phenyl]methylidene] derivatives (07USA2007/ 0117798, 08USA2008 /0207900). 

The betaine anhydro-2-hydroxy-8-methyl-4-oxo-3 -phenyl-4//- imidazo[2,1 -b ][ 1,3]thi-azinium hydroxide undergoes thermal rearrangement to 2,3-dihydro-7-hydroxy-2-methyl-5-oxo-6-phenyl-3(2H),5H-pyrrolo[l,2-c]imidazolethione. A process involving an initial fission of the 1,2-bond and electrophilic ring closure of the resultant ketene intermediate into the 4-position of the imidazole nucleus is most likely involved in the rearrangement (equation 67) (80JOC2474). 

N-(4-Dimethylamino-phenyl)- E16a, 96 [- N(OH) - N = NH-Spalt.] N-Methyl-N-[2-(2-pyridyl)-ethy]]-E16a, 128 (R-NH-OH + En) N-Methyl-N-[2-(4-pyridy )-ethyl]-E16a, 129 (R-NH-OH + En) Imidazol 4(5)-(l-Hydroxy-cyclo-pentyl)- E8c, 157 (Br-imidazol/... 

H-Purin 6-Hydroxy-2-methyl-7-phenyl- E9b/2, 377 [5-COOR-4-(NH — Ac) — 1-Ar — imidazol + NH3]... 

Imidazol 5-Acetyl-2-(4-chlor-phenyl)-1 -hydroxy-4-methyl-E8c, 21 [H3C-CO-C(CO-CH3) = N-OH + Ar-CHO/ NH3]... 

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