4- Benzoylamino-3-phenyl

Bei der Oximierung von 3-Benzoyl-5-phenyl-l,2,4-oxadiazol wird ein Gemisch aus 3-( -Hydroximino-benzyl)-5-phenyl-l,2,4-oxadiazol (III 33%) und 4-Benzoylamino-3-phenyl-fura-zan (V 57%) erhaltcn107 ... 

Aus Hydroximino-phenyl-acetonilriloxid kann 4-Benzoylamino-3-phenyl-furazan entstehen moglicherwei-se wird im ersten Reaktionsschritt mit Benzonitril 3-(a-Hydroximino-benzvl)-5-phenyl-1,2,4-oxadiazol gebildet111 113-114. 

Nitro-cyclohexyl- 372 Nitro-phenyl- 372 Phenoxy-phcnyl- 601 Pheny[-(4-benzoylamino-phenyl)-... 

Phenyl-l,3-benzotellurazole 5.0 g (20 mmol) of 2-aminophenyl ethyl tellurium and 5 ml of triethylamine are dissolved in 20 ml of dichloromethane and the solution is cooled in an ice/water bath. 3.5 g (25 mmol) of benzoyl chloride dissolved in 10 m/ of dichloromethane arc added dropwise to the cooled solution of the tellurium compound and the mixture is stirred for 2 h. The crude 2-(N-benzoylamino)-phenyl ethyl tellurium is isolated, placed in 20 ml of phosphoryl chloride, and the mixture is heated under reflux for 3 h. After being cooled in an ice/water bath, the mixture is carefully hydrolyzed with an aqueous base and treated with sodium disulfite. The basic mixture is extracted with dichloromethane, and the extract is dried and concentrated under vacuum. The residue is chromatographed on a column of silica gel with hexane as the mobile phase and the product is recrystallized from hexane yield 0.9 g (15%) m.p. 118-120°. Similarly prepared were ... 

Benzoylamino)phenyl methyl ketone oxime (2.54 g, 10 mmol) was dissolved with stirring in 85% HjSO (15 mL). The solution was warmed for 15 min to 80-90°C whereby its color changed to orange and subsequently to red. The mixUrre was poured into H O (250 mL) and the crystals which separated were filtered off, washed with NaHCO, and water, and recrystallized from 50% EtOH yield 2.05 g (88%) mp 134- 137 °C. 

Aus dem gemischten Anhydrid des N-Benzoyl-DL-phenylalanins wird in ahnlicher Weise 2-Benzoylamino-3-phenyl-propanol erhalten. Das mildere Reduktionsmittel Na-triumboranat wird z.B. zur Herstellung des amorphen 6-Phenylacetamino-penicillanyl-al-kohols3 eingesetzt. 

Analog erhalt man aus 5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol 2-Benzoylamino-athanol5 (88% d.Th.) und mit Lithiumalanat aus 5-Oxo-4-methyl-2-benzyliden-2,5-dihydro-1,3-oxazol 2-Phenylacetylamino-propanol (30% d.Th.)6. Calciumboranat reduziert 5-Oxo-2-phenyl-4-benzyliden-4,5-dihydro-1,3-oxazol zu oc-Benzoylamino-zimtal-kohol1. 

The treatment of (2-benzoylamino-5-iodobenzoyl-amino)acetic acid ethyl ester 88 with hydrazine hydrate for 4h yielded hydrazine derivative 2-benzoylamino-iV-hydrazinocarbonylmethyl benzamide 89, which on refluxing with sodium acetate and acetic acid for 8 h resulted in the formation of 6-iodo-10-phenyl-3//-3,4,9,10a-tetra-azaphenanthren-2-one 90 <2000IJH59> (Scheme 5). 

Fig. 10.23 X-ray structure of [Rh((R,R)-Et-DuPHOS)((Z)-3-N-acetylamino-3-(phenyl)-methyl propenoate)]+ and of[Rh((S,S)-DIPAMP)((Z)-2-benzoylamino-3-(3,4-dimethoxyphenyl)-methyl acrylate)]+ [62],...

A few examples, illustrating the principle of this type of degenerate rearrangement, are the thermo-induced equilibrium shift of 3-benzoylamino-5-methyl-l,2,4-oxadiazole into 3-acetylamino-5-phenyl-l,2,4-oxadiazole and the isomerization of 5-benzoyl-methylfuroxan oxime into 4-[a-nitroethyl]-3-phenylfurazan (82G181) (Scheme 1.8). They are extensively discussed in Chapter IV. 

One of the earlier examples of a degenerate ring transformation involving the participation of a three-atom side chain is the interconversion of the isomers 3-benzoylamino-5-methyl-l,2,4-oxadiazole (133, X = H) and 3-acetylamino-5-phenyl-l,2,4-oxadiazole (134, X = H) (Scheme IV.51) (75JHC985 89H(29)737). Heating each of these compounds at 181°C furnished an identical equilibrium mixture of isomers, in which mixture isomer 134 (X = H) is predominant (X134/133 at 181°C is about 6.4). These data indicate that the conversion of isomer 133 (X = H) into 134 (X = H) is dri-... 

Unsubstituted species 114a is prepared from tropone 112 by cyclization with formamide (61BCI312) or with ethoxymethylene acetates and pyrolysis of intermediate oxazolines 115e-g (60NKZ509 61BCJ611). 2-Phenyl derivative 114d is obtained from 2-methoxy-7-(benzoylamino)tropone with... 

Irradiation of a benzene solution of anhydro-4-benzoylamino-2-phenyl-l,3-dithiolium hydroxide (141, R = Ph, R = H, R = COPh) yields the 1,2-dithiole (145, 80%). This photoisomerization has been interpreted as involving the bicyclic intermediate 144. ... 

No loss of optical purity was observed in the mild acidic hydrolysis of the enantiomerically pure 6-alkoxy -phenyl-5,6-dihydro-4/7-l,3-oxazine 132, which resulted in formation of (R)-3-benzoylamino-3-phenylpropanal 133 in excellent yield (Scheme 20). Hydrolysis of the analogous tetrahydro-l,3-oxazin-2-one 134 to 133 required a stronger acidic medium and took place only in poor yield, but without any decrease in the optical purity <20000L585, 2003JOC4338, 2004TL9589>. 

The ring-opening reactions of l,3-oxazin-6-ones with nucleophiles or electrophiles both result in / -amino acid derivatives. Methanolysis of 2-phenyl-4,5-dihydro-l,3-oxazin-6-one 206 under very mild conditions gave methyl 3-(benzoylamino)propionate 207 (Equation 19) <20030L1575>. 

Similarly, reaction of 2-dimethylaminomethylene-3-oxoalkanoates or 2-di-methylaminomethylene-1,3-cyclohexanediones with 2-phenyl-5(4/7)-oxazolone 146, generated in situ from hippuric acid, affords 6-substituted 3-(benzoyl-amino)-2-oxo-2//-pyran-5-carboxylates 204 and 3-(benzoylamino)-7,8-dihydro-2//-l-benzopyran-2,5(6//)-diones 206, respectively. These compounds showed strong local anesthetic activity (Scheme 7.62). ... 

The first attempt to prepare 2-phenyl-4-(phosphoranylidene)-5(4//)-oxazolone 219 started with l-benzoylamino-(2,2-dichloroethenyl)triphenylphosphonium chloride 216 and involved the complex reaction sequence shown in Scheme 7.67. The structure and properties of 219 were studied and it was shown that 219 underwent Wittig olefination with benzaldehyde to give the well-known (Z)-4-benzylidene-2-phenyl-5(477)-oxazolone. ... 

Analog reagiert 4-Amino-3-phenyl-furazan mit Chrom(VI)-oxid in Eisessig (Bis-[4-phenyl-furazan-3-yl -diazen)265 3-Benzoylamino-4-amino-furazan laBt sich mit Brom/Natronlauge zur Azo-Verbindung (Bis-[4-benzoylamino-furazan-3-yl]-diazen) umsetzen263. 

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