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1-(2-Quinolyl)-3-aryl-4,7-phenanthrolines were synthesized by reacting arylidene-6-quinolylamines with 2-acetylqidnoline in n-butanol in the presence of hydrochloric acid. It was found that the formation of the 4,7-phenanthroline ring is preceded by the stage of formation of an intermediate aminoketone, 1-(2-quinolyl)-3-phenyl-3-(6-quinolylamino)propan-1-one. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.

Catalytic hydroamination of 1,2-bis-(hydroxymethyl)cyclohexane by aliphatic nitriles over a nickel catalyst yielded a series of N-alkyl-substituted octahydroisoindoles. Conditions for their synthesis were selected. The IR, PMR, and mass spectra and the probable mechanism of formation of these compounds are discussed.

8. M. D. Mashkovskii, Drugs [in Russian], Vol. i, Moscow (1986), p. 400. 9. V. I. Pantsurkin and V. S. Shklyaev, Recent Problems in Pharmaceutical Science and Practice [in Russian], Ashkhabal (1976), p. 134. i0. Austrian Pat. 213396, 1961; Ref. Zh., Khim., No. 24, L 325 (1961). ii. N. T. Pryanishnikova and V. A. Pchelin, Dokl. Akad. Nauk SSSR, 126, No. 6, 1358-1371 (1959). 12. N. T. Pryanishnikova, Pain and Its Control [in Russian], Sverdlovsk (1966), pp. 181-184. 13. V. S. Shklyaev, V. I. Pantsurkin, N. I. Vakhrina, and M. I. Vakhrin, Khim.-farm. Zh., No. 4, 49-55 (1980). 14. V. S. Shklyaev, V. I. Pantsurkin, V. N. Ryazanov, and N. I. Vakhrina, Zh. Obshch. Khim., 53, No. 6, 153-157 (L983). 15. D. Beke, K. Lempert, and I. Gyermek, Acta Chim. Acad. Sci. Hung., ~, No. 1-2, 143-149 (1954). 16. F. Bovet-Nitti andP. Bovet, Arch. Int Pharmacodyn., 96, No. 3-4, 327-355 (1954). 17. N. L. Cerden and I. E. Steinhaus, Circulat. Res., No. 4, 680 (1956). 18. O. Exner, Collect. Czech. Chem. Commun., 31, 65 (1966). 19. C. Hansch, A. Leo, S. H. Unger et el. J. Med. Chem., 16, No. Ii, 1207-1216 (1973). 20. N. Lofgren and I. Fischer, Svensk. Kem. Tid., 58, 219-231 (1946). 21. N. Lofgren, N. Lungvist, and S. Lindstrom, Acta Chem. Scand., 9, No. 7, 107941085 (1955).

Diffuse reflection electronic spectroscopy and ESR spectroscopy have been used in a study of the valence and coordination state of vanadium ions in vanadium-alumina and vanadium-magnesia catalytic systems that are effective in the oxidative dehydrogenation of hydrocarbons. On the surface ofγ-Al2O3, vanadium ions in octahedral coordination with the oxygen of the immediate surtoundings may be grouped primarily in clusters of 10–12 ions, providing stability of the V5+ ions against reduction to lower degrees of oxidation, and also providing easy reoxidizability of V4+ at ∼20°C. On the surface of MgO, the vanadium ion clusters that are formed are mostly small — two or three ions. Modification with KOH, K2SO4 and CdO tends to stabilize the V5+ under the reaction conditions in the oxidative dehydrogenation of ethylbenzene to styrene in the presence of nitrobenzene.

1-(2-Quinolyl)-3-aryl-4,7-phenanthrolines were synthesized by reacting arylidene-6-quinolylamines with 2-acetylqidnoline in n-butanol in the presence of hydrochloric acid. It was found that the formation of the 4,7-phenanthroline ring is preceded by the stage of formation of an intermediate aminoketone, 1-(2-quinolyl)-3-phenyl-3-(6-quinolylamino)propan-1-one. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.

Catalytic hydroamination of 1,2-bis-(hydroxymethyl)cyclohexane by aliphatic nitriles over a nickel catalyst yielded a series of N-alkyl-substituted octahydroisoindoles. Conditions for their synthesis were selected. The IR, PMR, and mass spectra and the probable mechanism of formation of these compounds are discussed.

This article reports on a study of the changes in physicochemical properties of the multimetal catalyst KR-104 over an operating period of four years in an LG-35-8/300B reformer. A disadvantage of multimetal catalysts is their high sensitivity to catalyst poisons. Data are presented on the variation of sulfur content in the feed and the sulfur and nitrogen contents in the reformate. Catalyst samples were taken from the reactors of the unit after oxidative regeneration and before chlorination. Catalyst samples taken after the fourth oxidative regeneration contained less sulfur than after the preceding regeneration. In oxychlorination, in addition to saturation of the catalyst with chlorine, there is a decrease in the dispersity of the platinum. It is concluded that the multimetal catalyst KR-104 has exceptional regeneration properties and high stability and catalytic activity. The platinum remains highly dispersed. Iron and sulfate sulfur accumulate in the KR-104 catalyst during service, as with the AP-56 and AP-64 catalysts. Includes a table.

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.

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.

The reaction of 3-[N-(2-naphthyl)formimidoyl]pyridine with substituted acetophenones in the presence of a proton catalyst leads to 1-aryl-3-(3-pyridyl)benzo[f]quinolines. Noncyclic amino ketones — [1-aryl-3-(3-pyridyl)-3-(2-naphthylamino)]-1-propanones — precede the formation of the cyclic products. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.

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.

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 (γ=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.

Pentamethylidynecyanine dyes were synthesized by the reaction of 1-methyl-3-(R-phenyl)benzo[f]quinolinium quarternary salts with 1,3,3-triethoxy-1-propene, Pentamethylidynecyanines substituted in the meso position of the polymethine chain were obtained by condensation of these salts with 1-anilino-2-methyl-3-dimethoxy-1-propene hydrobromide. The spectral and generational characteristics of the dyes were determined. It was shown that the presence of a phenyl group in the benzo-[f]quinoline ring of the dyes gives rise to a bathochromic shift of the absorption and generation maxima. The investigated dyes have high generation efficiencies that lie in the 20–30% range and in the 940–1010 nm spectral range.

Thermal desorption studies of benzene from γ-Al2O3 and 0.3 wt. % Al2O3-supported Pd catalysts have revealed substantial differences not only in the CO content but also in the temperature ranges of its desorption for the carrier and catalyst. The identified thermal desorption products are benzene, H2O, and CO2.

Condensation of p-methoxybenzylidene-2-naphthylamine with methyl ethyl ketone leads to a mixture of 1-ethyl- and 1,2-dimethyl-3-(p-methoxyphenyl)benzo[f]quinolines, for which protic and quaternary salts were obtained. Cyanine dyes were synthesized from 1,2-dimethyl-3-(p-methoxyphenyl)benzo[f]quinoline methiodide.

1. Incorporation of cations of alkali elements and rare earths into aluminum-chromium catalysts after their reduction reduces the Cr(II) content in comparison with catalysts without such additives; this is due to ordering of the chromic oxide structure, leading to a decrease in the number of surface chromium ions. 2. The chemical change in the surface of oxidized aluminum-chromium catalysts after incorporation of potassium ions has little effect on the Cr(II) content. 3. The Cr(VI) ions are distributed throughout oxidized aluminum-chromium-calcium catalysts, and are not located only on the surface.

The catalytic interaction of 5-acetylacenaphthene with arylidene-2-naphthylamines leads to the formation of adducts to the C=N bond (aminoketones) or 1-(5-acenaphthenyl)-3-aryl-(heteroaryl) benzo[f]quinolines. In several instances they are accompanied by 1-(5-acenaphthenyl)-3-R-2-propen-1-ones or N-substituted 2-naphthylamines. The ratio of the products depends on the condensation conditions and the structure of the starting azomethine. Using the 3-(p-fluorophenyl)-substituted derivative as an example, it has been shown that in the absence of dihydrogenating agents Β-aminoketones undergo dehydrocyclization with formation of benzoquinolines and 1,2,3,4-tetrahydroquinolines.

Platinum dispersity and catalytic activity of L-zeolite-metal catalysts at 773 K have been studied depending on the nature of a modifying agent. The mean size of Pt particles is shown to decrease by a factor of 1.5–2 upon adding Re or W. No relation between Pt dispersity and activity in n-hexane dehydrocyclization has been revealed.

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.

Reaction of furfuryl and tetrahydrofurfuryl alcohols with nitriles over copper oxide catalysts under a hydrogen pressure of 15 atm at a temperature of 230‡C gives N-alkylfurfuryl- (yield 46–50%) and N-alkyl-tetrahydrofurfurylamines (49–53%), and N-alkylpiperidines (28–41%). A reaction mechanism is proposed.

Amino derivatives of 1,3-diarylbenzo[f]quinoline were synthesized and subjected to reaction with methyl vinyl ketone in the presence of catalytic amounts of concentrated HCl to give the corresponding (3′-oxobutyl) aminophenyl derivatives. The electronic absorption and fluorescence spectra were studied, and the absolute fluorescence quantum yields of the synthesized compounds were determined. A relationship between the position and intensity of the absorption bands and the electron-donor substituents was uncovered, and a substantial effect of the nature of the solvent on the fluorescent spectra was established.

It was established on the basis of a study of the mass spectra of benzo[f]quinoline derivatives that contain a methyl group or an aromatic or heterocyclic ring in the 1 position and various quinolyl groups (2-, 4-, and 6-quinolyl) in the 3 position that the geometry of the molecule has a decisive effect on the strength of the chemical bond between the substituents and the benzoquinoline ring. The degree of coplanarity of the heterocyclic rings determines the strength of interannular conjugation and consequently the strength of the bond between the rings. For the investigated polyheterocyclic systems the coplanarity increases in the order 2-quinolyl < 6-quinolyl < 4-quinolyl. This fact in turn has a strong effect on the pathway of mass-spectrometric fragmentation for each series of derivatives, and this makes it possible to reliably distinguish the 2-, 4-, and 6-quinolyl derivatives from their mass spectra.

Azomethine dyes were obtained by reaction of 1-methyl- and 1,2-dimethyl-3-arylbenzo[f]quinolinium methiodides with 1-nitroso-2-naphthol. Merocyanine dyes were isolated by the action of KOH on 2-hydroxy-5,6-benzostyryl derivatives of 3-arylbenzo[f]quinolinium salts. The absorption spectra of the dyes in ethanol and chloroform are presented, and it is shown that, as compared with the spectra of the merocyanines, there is a bathochromic shift of the absorption bands in the spectra of the azomethine dyes. The azomethine and merocyanine dyes have solvatochromic properties and display photosensitivity in the UV and visible regions when they are introduced into a polymer matrix.

1-(3-pyridyl)-3-aryl-8-aminobenzo[f]quinolines were synthesized by reduction with tin in acidic media of 1-(3-pyridyl)-3-aryl-8-nitrobenzo[f]quinolines obtained by catalytic condensation of arylidene(6-nitro)-2-naphthylamines with acetylpyridine. The structures of the compounds were proved by a set of data from elementary analysis and IR, UV, and mass spectroscopy. The change in the luminescence of 1-(3-pyridyl)-3-aryl-8-aminobenzo[f]quinoline as a function of the solvent was studied.

A new series of indoloquinoline derivatives was obtained by catalytic condensation of carbazole-containing azomethines with acetone. It was shown by means of a combination of physicochemical methods of investigation (UV, IR, NMR, and mass spectroscopy) that the synthesized compounds have angular structures.

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.

A study has been made of the physicochemical and catalytic properties of vanadium-containing oxide systems in the process of combined production of styrene and aniline. It has been shown by spectroscopic methods that octahedrally coordinated vanadium(V) and (IV) ions participate in the active centers.

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 α,β-unsaturated ketones, were isolated. The IR, UV, PMR, and mass spectra of the synthesized compounds are discussed.

Cyclic ketones react with N-(2-naphthyl)formimidoyl-4-pyridine in refluxing aliphatic alcohol to form 1,2-(1′,2′-cycloalkylene)-3-(4-pyridyl)benzo[f]quinolines. Under mild conditions, cyclopentanone and cyclohexanone gave dihydrobenzo[f]quinoline derivatives — 1,2-(1′,2′-cycloalkylene)-3-(4-pyridyl)-3,4-dihydrobenzo[f]quinolines, whereas cycloheptanone gave an aminoketone — 2-[(4-pyridyl) (2-naphthylamino)methyl]cycloheptanone.

Studies of the disproportionation of toluene on ultrastable Y zeolites have revealed that the incorporation of Pd into Cr containing zeolite at 400°C increases its catalytic activity and stability.

Ethyl cyclopentanonecarboxylate reacts with Schiff bases to give amino keto esters, from which 5,6-benzoquinoline derivatives are synthesized in the presence of hydrochloric acid. Compounds of the enamine type are obtained in the presence of acetic acid.

1. The effect was investigated of additions of rare-earth elements on the properties of alumino-platinum catalysts in gasoline-reforming reactions. 2. It is found that alumino-platinum catalysts promoted by rare-earth elements have greater activity, selectivity, and thermal stability in comparison with unpromoted samples.

The dehydrogenation of cyclohexylamine on platinum catalysts is investigated. In addition to aniline and diphenylamine, significant amounts of carbazole are formed. A possible mechanism for its formation is proposed.

1. Platinized alumina catalysts promoted with REE are more resistant to the action of nitrogen compounds. 2. The REE ions exert a partial stabilizing effect on the acid centers of the aluminum oxide.

Oxidation of 4-styryl-2-phenyl-5,6-benzoquinoline with potassium permanganate gave phenyl 2-phenyl-5,6-benzo-4-quinolyl diketone, 2-phenyl-4-formyl-5,6-benzoquinoline, 2-phenyl-5,6-benzocinchoninic acid, and benzoic acid. It is shown that phenyl 2-phenyl-5,6-benzo-4-quinolyl diketone is cleaved under the influence of OH− ions to the corresponding aldehydes and carboxylic acids; this is explained by the decisive effect of the acidity of the media on the direction of the reaction.