Synthesis of 1,3-diaryl-4,7-phenanthrolines

Kozlov, N. S.; Gusak, K. N.; Serzhanina, V. A.; Krot, N. A.

doi:10.1007/bf00515259

Cited by 5 publications

(17 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the basis of the catalytic condensation of azomethines of the 6-aminoquinoline series with CH acids effective methods were developed for the production of 4,7-phenanthrolines 31 -the diaza analogs of benzo[f]quinoline systems [39][40][41][42]. It was shown that the reaction of arylmethylidene-6-quinolylamines with acetophenone and its para-substituted derivatives, 3-acetylpyridine, and 2-acetylquinoline in an aliphatic alcohol in the presence of HCl takes place through the stage of the formation of intermediate β-amino ketones of the quinoline series 32.…”

Section: Synthesis Of Derivatives Of 47-phenanthrolinementioning

confidence: 99%

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Козлов¹,

Gusak²,

Kadutskii³

2010

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

Section: Synthesis Of Derivatives Of 47-phenanthrolinementioning

confidence: 99%

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Козлов¹,

Gusak²,

Kadutskii³

2010

Chem Heterocycl Comp

Self Cite

View full text Add to dashboard Cite

“…The synthesized alkylphenoxycarbonyl benzo[b]- [4,7]phenanthroline derivatives Va3Vc and VIa3VIc are colorless or light yellow crystalline substances…”

mentioning

confidence: 99%

“…Among possible intermediates A3D, the key species is amino keto enol C undergoing cyclocondensation to phenoxycarbonyl-substituted benzo[b] [4,7]phenanthroline. Amino keto enol C can form either by addition of the intermediate arylmethylenephenidone A to 6-quinolylamine at the 5-C atom of the quinolyl ring, bearing the highest electron density [5], or by rearrangement of amino hydroxy ketone D following the pattern of the Hofmann3Martius rearrangement [6].…”

mentioning

confidence: 99%

“…

Vanillin and vanillal (4-hydroxy-3-metoxy-and 4-hydroxy-3-ethoxybenzaldehyde), which are plant phenols, are widely used as fragrant additives in food industry, perfumery, and cosmetics, and also as versatile reagents in organic synthesis [1,2].

…”

mentioning

confidence: 99%

“…Previously unknown 2-methoxy(or ethoxy)-4- (11-oxo-9-phenyl-7,8,9,10,11,12-hexahydrobenzo-[b] [4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids were prepared by ternary condensation of vanillin or vanillal alkanoates with 6-quinolylamine and Phenidone. According to the 1 H NMR spectra, the target products are formed as mixtures of diastereomers.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Reactions of Vanillin and Vanillal Esters with 6-Quinolylamine and Phenidone

Gusak

Козлов

2005

Russ J Gen Chem

Self Cite

View full text Add to dashboard Cite

Previously unknown 2-methoxy(or ethoxy)-4- (11-oxo-9-phenyl-7,8,9,10,11,12-hexahydrobenzo-[b] [4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids were prepared by ternary condensation of vanillin or vanillal alkanoates with 6-quinolylamine and Phenidone. According to the 1 H NMR spectra, the target products are formed as mixtures of diastereomers.Vanillin and vanillal (4-hydroxy-3-metoxy-and 4-hydroxy-3-ethoxybenzaldehyde), which are plant phenols, are widely used as fragrant additives in food industry, perfumery, and cosmetics, and also as versatile reagents in organic synthesis [1,2]. In particular, vanillin and vanillal can be modified by esterification of the hydroxy group with chlorides or anhydrides of organic acids of various classes. The resulting vanillin and vanillal derivatives contain both ether and ester groups. Reactions of such compounds with arylamines and CH acids open prospects for preparing biologically active condensed nitrogen-containing heterocycles with alkoxy and alkylcarboxy fragments [3,4]; these fragments increase the solubility of the compounds in aqueous alcohol and extend the possibilities of biological testing and application.We showed in [4] that vanillin alkanoates react with 6-quinolylamine and 1,3-cyclohexanedione to form 2-methoxy-4- (11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids; with dimedone taken instead of 1,3-cyclohexanedione, the corresponding 9,9-dimethyl derivatives are formed.In this study, with the aim to prepare new compounds of this class, we performed condensation of vanillin and vanillal alkanoates Ia3Ic and IIa3IIc with 6-quinolylamine III and 5-phenylcyclohexane-1,3-dione (Phenidone) IV.Esters Ia3Ic and IIa3IIc were prepared in 80 390% yields from the corresponding acid chlorides and vanillin or vanillal, by refluxing in CH 2 Cl 2 in the presence of pyridine.The condensation of Ia3Ic and IIa3IIc with III and IV was performed by refluxing the equimolar amounts of the reactants in 1-butanol without catalyst.The desired 2-methoxy(or ethoxy)-4-(11-oxo-9-phenyl-7, 8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl)phenyl esters of carboxylic acids Va3Vc and VIa3VIc were thus prepared in 58370% yields. The compounds, according to the NMR spectra, are approximately equimolar mixtures of two diastereomers differing in the position of the phenyl group at C 9 (pseudoaxial or pseudoequatorial).The target products Va3Vc and VIa3VIc can form by different pathways depending on the order in which the components react with each other. Among possible intermediates A3D, the key species is amino keto enol C undergoing cyclocondensation to phenoxycarbonyl-substituted benzo[b] [4,7]phenanthroline. Amino keto enol C can form either by addition of the intermediate arylmethylenephenidone A to 6-quinolylamine at the 5-C atom of the quinolyl ring, bearing the highest electron density [5], or by rearrangement of amino hydroxy ketone D following the pattern of the Hofmann3Martius rearrangement [6]. In turn, intermediate D is f...

show abstract

Oxidation of 4,7-phenanthroline derivatives

2004

Self Cite

View full text Add to dashboard Cite

Oxidation of 1,3-diphenyl-4,7-phenanthroline with potassium permanganate in alkaline medium results in transformation of the 4,7-phenanthroline ring system into 1,8-diaazafluorenone. Oxidation of 12-aryland 12-aryl-9, 9-dimethyl-8,9,10,12-tetrahydro-7H-benzo[b][4,7]phenanthrolin-11-ones (condensation products of 6-arylmethylene-aminoquinolines with 1,3-cyclohexanedione and dimedone) with sodium nitrite in acetic acid leads to 12-aryl-9,10-dihydro-8H-benzo[b] [4,7]phenanthrolin-11-ones. 13-Aryl-7,13-dihydro-12H-indeno-[2,1-b][4,7]phenanthrolin-12-ones obtained by reaction of 6-arylmethyleneaminoquinolines with 1,3-indandione are oxidized to 13-aryl-12H-indeno[2,1-b][4,7]phenanthrolin-12-ones on heating in nitrobenzene.

show abstract

Synthesis of 1,3-diaryl-4,7-phenanthrolines

Cited by 5 publications

References 4 publications

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

Reactions of Vanillin and Vanillal Esters with 6-Quinolylamine and Phenidone

Oxidation of 4,7-phenanthroline derivatives

Contact Info

Product

Resources

About