Benzimidazole 5-phenoxy

Dichlor-diphenoxy-methan (Herstellung s. Lit.95) wird in der Benzimidazol-Chemie als Synthon fur Kohlensaure-cyanimide eingesetzt, die weiter zu 2-Cyanamino-benzimidazolen cycli-siert werden (s. S. 230f.). Mit 1,2-Diamino-benzol wird 2-Phenoxy-benzimidazoI (52% Schmp. 220-222°) erhalten280... 

Eine etwas niedrigere Ausbeute an 5(6)-Phenoxy-benzimidazol (65%) crzielt man beim Erhitzen der beiden Komponenten in 4 N Salzsaure (Philipps-Reaktion)238,... 

Methoxycarbonyl-phenoxy)-methyl]-benzimidazol 88% Schmp. 159-159,5° Die Carbonsaure-ester-imide konnen auch in absol. Ethanol in situ erzeugt werden166 z.B. ... 

Syntheses of phenoxy-substituted polynaphthylimides and polyperyleneimides were carried out in accordance with Scheme 5.4 [37, 38]. All polycondensation reactions were carried out under high-temperature solution polycondensation conditions in phenolic solvents (w-cresol, m- or p-chlorophenols) using benzimidazole and benzoic acid as catalysts. All the reactions proceeded homogeneously and led to the formation of deeply coloured polymers. General properties of the polymers are listed in Table 5.6. 

There are reports that benzimidazoles can be made by eyclization of N-arylimidoyl nitrencs generated by photolysis of sulfimides of 1-aryltetrazoles [3, 4]. These should be compared to the related imidazole synthesis in Section 6.1.2.3. Examples include the formation of 2-phenylbenzimidazole (42%) from 1,5-diphenyltetrazoIe [5], and 5-phenoxybenzimidazole (36%) from 5-phenoxy-l-phenyltetrazole [6]. These reactions have little apparent synthetic importance. 

N- 2-[4-(lH-Benzimidazole-2-yl)phenoxy]ethyl)substituted amine derivatives Bis(9)-(-) -nor-meptazinol Diazapentacyclic analogs Donepezil-hydrazinonicotinamide hybrids Dual drugs (cholinesterase inhibitors + MAO inhibitors)... 

Benzimidazol-Bildung wird auch bei der Photolyse von 5-Phenoxy-l-phenyl-lH-tetrazol beobachtet1 ... 

Also, on chelation to a benzimidazole the heterocyclic system is not planar as shown by the crystal data of 4-phenoxy-l/4,2,4,6-thiatriazino[4,3-sulfur atom lies visibly out of the best plane of the ring system. Even in solution thiatriazinobenzim-idazoles exhibit nonplanarity, as shown by the H NMR of jV-tosyl-4-(2,2,2-trichloroethoxy)-l/4,2,4,6-thiatriazino 4,3-<7]benzimidazol-2-amine (see Section 2.1.1.1.2., compound 3d). The CH, moiety of the 2,2,2-trichloroethoxy group in the 4-position gives an AB quartet defining the chirality of the sulfur atom.54... 

Phenoxy-/V-(phenylsulibnyl) 124,2,4,6 thiatriazino 4,3- ]benzimidazol-2-amine (3a) Typical Procedure 14 54... 

Annulated systems such as 4-phenoxy-124,2,4,6-thiatriazino[4,3-a]benzimidazole 2-oxide or 124,2,4,6-thiatriazino[2,3-a]benzimidazol-3-amine 1-oxides are readily oxidized with periodate in aqueous solution3 to the corresponding 5,5-dioxides 4 and 5. 

Two different binuclear copperdi) complexes have been prepared recently, one with a bridging phenoxy ligand having two bis-benzi-midazole arms (12, Fig. 14), and the second having a bis-cyclen-naphthalene ligand (13, Fig. 15) (352, 353). Both of them show bimetallic cooperativity for the hydrolysis of phosphate diesters, contrary to studies with the dinuclear cobalt complex (354). The pseudo-first-order rate constants for hydrolysis of the para-nitrophenylphosphate ester of propylene glycol by bis-benzimidazole-based copper complexes... 

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