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

A number of new 1,3-diaryl-4,7-phenanthrolines were synthesized by heterocyclization of arylidene-6-quinolylamines with acetophenones in the presence of an acidic catalyst. Intermediate amino ketones and side products, viz., N-(R¹-benzyl)-6-quinolylamines and ,-unsaturated ketones, were isolated. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1398–1401, October, 1985.     

Reaction of arylidene-2-naphthylamines with the ethyl ester of (2-quinolyl)-β-oxopropionic acid

The reaction of arylidene-2-naphthylamines with the ethyl ester of (2-quinolyl)--oxopropionic acid results in the synthesis of ethyl esters of 1-(2-quinolyl)-3-arylbenzo[f]quinoline-2-carboxylic acids. All the theoretically possible intermediate reaction products were isolated: the amino esters of 2-quinoline--oxopropionic acid, the hydroxy esters of tetrahydro- and esters of dihydrobenzo[f]quinoline-2-carboxylic acid, as well as the by-products — the ethyl ester of 2-quinolyl--(R-benzylidene)--oxopropionic acid. The IR, UV, and mass spectra of the synthesized compounds are discussed.Institute of Physical Organic Chemistry, Belorussian Academy of Sciences, Minsk 220603. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1406–1410, October, 1994. Original article submitted October 5, 1994.     

Spectral luminescence properties of 1- and 2-alkyl(cycloalkyl) derivatives of benzo[f]quinoline

The absorption and fluorescence spectra of alcohol solutions of 3-aryl-substituted benzo[f]-quinolines were investigated, and the fluorescence quantum yields were measured. It was established that the indicated compounds have intense absorption in the UV region and fluorescence at 350–450 nm. The fluorescence quantum yields range from 5 to 70%, depending on the substituents. The introduction of aromatic substituents in the 1 and 3 positions of benzo-[f]quinoline ring raises the fluorescence quantum yields. A methyl group in the 2 position of the molecule leads to a decrease in the fluorescence quantum yield. Benzo[f]quinoline derivatives that contain a cyclopentene ring in the 1 and 2 positions fluoresce intensely (=40–60%), while cyclohexene and cycloheptene condensed in the same positions cause a decrease in the fluorescence yield to 7–13%; this is associated with the three-dimensional structure of these molecules.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1237–1240, September, 1977.     

Effect of a pyridine substituent on spectral characteristics of benzo[f]quinolines with an annelated alicyclic ring

Reaction of N-(2-naphthyl)formimidoyl-3-pyridine with cyclic ketones leads to the formation of 1,2-cycloalkyleno-3-(3-pyridyl)benzo[f]quinolines. Aminoketones, namely, 2-[(3-pyridyl)(2-naphthylamino)methyl]cycloalkanones, are intermediates in this reaction. The absorption-luminescence, PMR, and mass spectra of these newly synthesized compounds have been investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1409–1413, October, 1989.     

Reaction of N-arylidene-2-naphthylamines with allylacetone

The reaction between N-arylidene-2-naphthylamines and allylacetone leads to the formation of 1,3-disubstituted benzo[f]quinolines having a butenyl radical in position 1. It is shown that the reaction proceeds via intermediate aminoketones — 1-(2-naphthylamine)-1-aryl-6-heptene-3-ones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1519–1522, November, 1986.     

Luminescence of dihydro derivatives of benzo[f]quinoline

The spectral luminescence properties of 3-aryl-3,4-dihydrobenzo[f]quinolines containing alicycles and ester groups in the 1 and 2 positions were investigated. It is shown that compounds of this type have intense luminescence (52–76%). The quenching effect of an ester group in the heterocyclic ring was established. The spectral luminescence characteristics of compounds with an ester group in the alicycle are determined by the proton-acceptor properties of the carbonyl function of this group. The effect of the solvent on the spectral luminescence characteristics of the investigated compounds is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 810–813, June, 1977.     

Reaction of arylidene-2-naphthylamines with ethyl furoylacetate

The reaction of arylidene-2-naphthylamines with ethyl furoylacetate was studied. It is shown that noncyclic amino keto esters are formed when the reaction is carried out without a catalyst and that esters of the benzo[f]quinoline series are formed when the reaction is carried out in the presence of a catalyst and an oxidizing agent. Esters of the benzo[f]quinoline series are also formed in the cyclization of the amino keto esters. The structures of the reaction products were confirmed by the results of elementary analysis and the IR, UV, NMR, and mass spectroscopic data.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 169–172, February, 1979.     

Spectral-luminescence characteristics of 1,3-diaryl-4,7-phenanthrolines

The effect of the nature of the substituents and the solvent on the absorption and fluorescence spectra and the fluorescence quantum yields of 1,3-diaryl-4,7-phenanthrolines was studied. Electron-donor groups in the para position of the phenyl ring cause a bathochromic shift of the absorption and fluorescence spectra and an increase in the fluorescence quantum yields. A change in the polarity of the solvent leads to a significant shift of the fluorescence spectra of hydroxy and dialkylamino derivatives of 4,7-phenanthroline.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1651–1654, December, 1987.     

Reaction of azomethines with acetoacetic ester

The reaction of (benzylidene) (2-naphthyl)amine with acetoacetic ester leads to ethyl 1-methyl-3-phenylbenzo [f]quinoline-2-carboxylate. Some reactions of this compound have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1082–1083, August, 1973.     

Spectral-luminescence and generation characteristics of 1-R-vinyl-3-aryl(heteryl)benzo[f]quinolines

The absorption and fluorescence spectra and the fluorescence quantum yields of 1-R-vinyl derivatives of benzo[f]quinoline containing aryl and 2-, 4-, and 6-quinolyl groups in the vinylene grouping and in the 3 position were studied. The relationship between the spectral-luminescence characteristics and the structures of the molecules was examined. It was established that solutions of compounds that contain a dimethylamino group attached to the phenyl ring give forced emission when they are excited with the second harmonic of a ruby laser. The effect of the solvent on the spectral-luminescence and generation characteristics of the indicated compounds was investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 511–515, April, 1978.