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Gusak, K. N.; Tereshko, A. B.; Козлов, Н. Г.

doi:10.1023/a:1013483424111

Cited by 10 publications

(6 citation statements)

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“…A solution of 5 mmol of phendione (I) and 5 mmol of azomethine IIIaIIIz, IIIa-IIIg in 20 ml of 1-butanol was boiled for 2.53 h. The reaction products IVaIVz, IVa-IVg and VIIaVIIz, VIIa-VIIg were isolated as described in procedure a. 9,2-Diphenyl-8,9,10,12-tetrahydro-7H-benzo-[b] [4,7]phenanthrolin-11-one (IVa, VIIa). Yield 54%, mp 291292°C.…”

Section: Methodsmentioning

confidence: 99%

“…Yield 54%, mp 291292°C. 1 12-(3-Hydroxyphenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-one (IVi, VIIi). Yield 65%, mp 327328°C.…”

Section: Methodsmentioning

confidence: 99%

“…The formed aminodiketone C suffers a hydramine cleavage into 6-quinolylamine and 2-arylmethylene-5-phenyl-1,3-cyclohexanedione A which react with each other as described above. Azomethines VIaVIz, VIa-VIg that we obtained in a preparative yield from 6-quinolylamine (II) and aldehydes IIIaIIIz, 8] cleanly react with phendione (I) under our conditions for three-component condensation to yield compounds IVaIVz, IVa-IVg. Inasmuch as we failed to isolate the intermediate products AC we believe that they take part in the presumed processes in situ.…”

mentioning

confidence: 88%

“…

AbstractBy condensation of 5-phenyl-1,3-cyclohexanedione with 6-quinolylamine and aldehydes of aromatic, heterocyclic, and cyclohexene series new 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-ones were prepared. The presence of diastereomers in the target reaction products was determined by 1 H NMR spectroscopy.

Cyclic b-diketones due to their high reactivity are widely used in the synthesis of fused nitrogen-containing heterocycles [14].

…”

mentioning

confidence: 99%

“…The condensation was performed by boiling at reflux of equimolar amounts or reagents in 1-butanol without catalyst. As a result 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-ones IVaIVz, IVa-IVg were obtained in 3276% yield.…”

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confidence: 99%

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Phendione in the Synthesis of Annelated Derivatives of 4,7-Phenanthroline

2005

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By condensation of 5-phenyl-1,3-cyclohexanedione with 6-quinolylamine and aldehydes of aromatic, heterocyclic, and cyclohexene series new 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-ones were prepared. The presence of diastereomers in the target reaction products was determined by 1 H NMR spectroscopy.Cyclic b-diketones due to their high reactivity are widely used in the synthesis of fused nitrogen-containing heterocycles [14]. Aiming at preparation of new biologically active 4,7-phenanthroline [5, 6] derivatives having two asymmetric carbon atoms we studied for the first time the reactions of phendione [5-phenyl-1,3-cyclohexanedione (I)] with 6-quinolylamine (II) and aldehydes of aromatic, heteroaromatic, and cyclohexene series IIIa IIIz, IIIa-IIIg. The condensation was performed by boiling at reflux of equimolar amounts or reagents in 1-butanol without catalyst. As a result 12-aryl(heteryl, cyclohexenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]-phenanthrolin-11-ones IVaIVz, IVa-IVg were obtained in 3276% yield.The formation of benzo[b]annelated products suggests that in the three-component reagents mixture first diketone I reacts with 6-quinolylamine (II) to give 5-phenyl-3-(6-quinolylamino)-2-cyclohexene-1-one (V) which further undergoes cyclocondensation with arylaldehydes IIIa IIIz, IIIa-IIIg into 4,7-phenanthrolines IVaIVz, IVaIVg. We isolated previously unknown aminoenone V in condensation of phendione (I) with 6-quinolylamine (II) and p-tolualdehyde IIId, but aminoenone V did not enter into the reaction with arylaldehydes under the given condensation conditions.The second possible pathway of 4,7-phenanthrolines IVaIVz, IVa-IVg formation consists in phendione (I) reaction with aldehyde IIIaIIIz IIIa-IIIg followed by the addition of the arising 2-[aryl(heteryl, cyclohexenyl)-methylene]-5-phenyl-1,3-cyclohexanedione A to 6-quinolylamine (II) at the carbon atom possessing the highest electron density and situated in position 5 of the quinoline structure and thereafter by cyclization of the aminodiketone B obtained.A reaction route thorough reaction between 6-quinolylamine (II) with aldehydes IIIaIIIz, IIIa-IIIg is also presumable affording arylmethylene-6-quinolylamines VIaVIz, VIa-VIg with further addition of phendione (I) to the C=N bond of the azomethine. The formed aminodiketone C suffers a hydramine cleavage into 6-quinolylamine and 2-arylmethylene-5-phenyl-1,3-cyclohexanedione A which react with each other as described above. Azomethines VIaVIz, VIa-VIg that we obtained in a preparative yield from 6-quinolylamine (II) and aldehydes IIIaIIIz, 8] cleanly react with phendione (I) under our conditions for three-component condensation to yield compounds IVaIVz, IVa-IVg. Inasmuch as we failed to isolate the intermediate products AC we believe that they take part in the presumed processes in situ.Aminodiketone B might arise as a result of intermediate C rearrangement through migration of an arylmethylenephendione fragment into the position 5 of t...

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Section: Methodsmentioning

confidence: 99%

“…Yield 54%, mp 291292°C. 1 12-(3-Hydroxyphenyl)-9-phenyl-8,9,10,12-tetrahydro-7H-benzo[b] [4,7]phenanthrolin-11-one (IVi, VIIi). Yield 65%, mp 327328°C.…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 88%

“…

Cyclic b-diketones due to their high reactivity are widely used in the synthesis of fused nitrogen-containing heterocycles [14].

…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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