Synthesis of benzo[g]quinoline derivatives

A method for the synthesis of 3-substituted benzo[g]quinolin-4-ones by the condensation of 1,2,3,4-tetrahydrobenzo[g]quinolin-4-one with aromatic aldehydes in an alkaline medium has been developed. It has been found that the first stage of the reaction is the formation of the corresponding benzylidene derivative, which then isomerizes into the more stable benzyl derivative. The structure of the 3-substituted benzo[g]quinolin-4-ones obtained, as existing in the tautomeric oxo form, is confirmed by their IR and UV spectra.For Communication VI, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinii, Vol. 6, No. 6, pp. 798–801, June, 1970.     

Synthesis of benzo[g]quinoline derivatives

4-Amino-substituted benzo[g]quinolines have been synthesized for the first time by the condensation of 4-oxo-1,2,3,4-tetrahydrobenzo[g]-quinoline with amines. This reaction is characterized by the addition of the amine, the splitting out of water, and the complete aromatization of the initial hydrogenated heterocyclic system. The UV spectra of the compounds obtained are similar to those of 4-amino-substituted quinolines, their maxima being displaced somewhat into the long-wave region.For part III, see [2].     

Synthesis of benzo[g]quinoline derivatives

The electronic spectra of linear benzo[g]quinoline, its 4-substituted derivatives, and some hydrogenated derivatives are examined and discussed.See [1] for communication IX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 662–665, May, 1972.     

Synthesis of benzo[g]quinoline derivatives

In the condensation of 1, 2, 3, 4-tetrahydro-4-oxobenzo[g]quinollne with ammonia, which leads to the formation of 4-aminobenzo[g]quinoline, the by-products are benzo[g]quinoline (V) and 1, 2, 3, 4-tetrahydrobenzo]quinoline (VI), which are also obtained from 1, 2, 3, 4-tetrahydro-4hydroxybenzo[g]quinoline by its dehydration and the subsequent disproportionation of the dihydrobenzo[g]quinoline formed.For communication II, see [1].     

Synthesis of benzo[g]quinoline derivatives

The synthesis of 4-aminobenzo[g]quinoline has been effected by the following three methods: 1) replacement of the halogen in 4-chlorobenzo[g]quinoline by an amino group; 2) dehydrogenation of the oxime of 1,2,3,4-tetrahydro-4-oxobenzo[g]quinoline; 3) direct condensation of 1,2,3,4-tetrahydro-4-oxobenzo[g]quinoline with ammonia.     

Synthesis of benzo [g]quinoline derivatives

The IR spectra of linear benzoquinoline derivatives at 700–900, 1400–1700, and 2800–3600 cm^–1 are discussed, and the characteristic frequencies are related to the peculiarities of the structures of the synthesized compounds.See [1] for communication VIIITranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 367–372, March, 1972.     

Synthesis of benzo[g]quinoline derivatives

It has been established that the cyclization of -(2-carboxy-3-naphthylamino)propionic acid into N-acetyl-4-oxo-1, 2, 3, 4-tetrahydrobenzo[g]quinoline takes place with the participation of acetic anhydride and an alkali metal acetate. In the absence of the alkali metal acetate cyclization takes place in a different direction. A mechanism for this reaction has been proposed as taking place through the formation of an internal mixed anhydride, which decomposes under the reaction conditions into N-acetyl-4-oxo-1, 2, 3, 4-tetrahydrobenzo[g]-quinoline and carbon dioxide.For part V, see [1].     

Synthesis of benzo[g]quinoline derivatives. XI. 2,4-Diamino-substituted benzo[g]quinolines

Previously unknown 2,4-diamino-substituted benzo[g]quinolines were synthesized from 2,4-dihydroxybenzo[g]quinoline.     

Synthesis of some benzo[h]quinoline derivatives

Reaction between 6-methoxy-1-tetralone, methyl propiolate and an ammonia-saturated methanolic solution led to 5,6-dihydro-8-methoxybenzo[h]quinolin-2(1H)-one in good yields. Subsequent aromatization, chlorination, substitution and demethylation enabled us to prepare 2-amino-substituted benzo[h]quinoline derivatives. These compounds, which are structurally related to the antitumor benzo[c]phenanthridine alkaloids by deletion of a ring, were tested on cultured murine lymphoblastic leukaemia cells (L1210). Results showed that they are devoid of cytotoxicity.     

Synthesis and spectral characteristics of acenaphthene derivatives of benzo[f]quinoline

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 -aminoketones undergo dehydrocyclization with formation of benzoquinolines and 1,2,3,4-tetrahydroquinolines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1102–1106, August, 1986     

Anthracene derivatives of benzo[f]quinoline. Synthesis,spectra, and luminescence

By condensation of 9-[N-(2-naphthyl)formimidoyl]anthracene with methyl ketones under conditions of acid catalysis, 1-R-3-(9-anthryl)benzo[f]quinolines have been obtained. The byproducts of the reaction have been identified: 1-R-3-(9-anthyl)-2-propen-1-ones and N-[1-(p-aminophenyl)-3-(9-anthryl)-2-propen-1-ylidene]-2-naphthylamines. The spectral and luminenscence properties of these compounds have been examined critically.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1536–1541, November, 1985.     

Synthesis of 4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1-cyclohexane) derivatives

The reaction of4-acylamino-3-cyano-1,2-dihydrospiro(naphthalene-2,1-cyclohexanes) with hydrogen chloride yields 2-substituted 4-oxo-3,4,5,6-tetrahydrospiro(benzo[h]quinazoline-5,1-cyclohexanes). It was found that when the latter are condensed with methyl iodide, N-alkylation takes place exclusively. Alkylation with ethyl iodide in analogous conditions yields a mixture of O- and N-substituted products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 658–661, May, 1992.     

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.     

Synthesis and luminescence of benzo[f]quinoline derivatives with fused alicyclic rings

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.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 947–950, July, 1986.     

Mass-spectrometric behavior of polynuclear derivatives of benzo[f]quinoline

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.Here and subsequently, the numbers that characterize the ion are the mass-to-charge ratios.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 520–526, April, 1979.     

7,8-亚甲二氧基-4-氧代-3,4-二氢嘧啶并[4,5-b]喹啉衍生物的合成

为了寻找具有药理活性的喹啉衍生物, 我们合成了五个新的喹啉衍生物和十一个7,8--亚甲二氧基-4-氧代-3,4-二氢嘧啶并[4,5-b]喹啉衍生物. 这些化合物的结构均经核磁共振光谱, 红外光谱和元素分析予以证实 .     

Synthesis of 1,2,3,4-Tetrahydro-4-oxothieno[3,2-d]pyrimidine and Perhydropyrimidine Derivates from Alkyl Dicyanoacetates

Nucleophilic addition of methyl 3-aminothiophene-2-carboxylate ( 2 ) as well as of β-alanine ethyl ester ( 11 ) to one CN group of the salts 1 of alkyl dicyanoacetates, followed by cyclization, yielded 1,2,3,4-tetrahydro-4-oxothieno[3,2-d]pyridimine derivatives 6 – 10 (Scheme 1) and perhydropyrimidine derivatives 17 – 19 (Scheme 2), respectively.     

Nitration of benzo[g]isoquinoline and its methyl-substituted derivatives

Di- and trinitro derivatives are formed in the nitration under mild conditions (0–5 °C) of benzo[g]isoquinoline and its analogs with a methyl substituent in the pyridine and phenylene rings. The principal reaction products contain a nitro group in the meso position (attached to the C₅ atom) and in the phenylene ring. The structures of the nitro derivatives obtained and the position of the nitro groups in the molecules were proved by means of the PMR, IR, and mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1658–1661, December, 1981.     

Heterocycles. Part XII. Synthesis of new benzo[6,7]cyclohepta[1,2-d]pyrimidine

Selected 2-arylidene-1-benzosuberones I were condensed with guanidine hydrochloride to give the corresponding substituted 2-aminopyrimidines II and III respectively. Condensation of chalcones I with benz-amidine hydrochloride revealed the formation of the corresponding substituted 2-phenylpyrimidines IV. The structure of all products was substantiated by chemical and spectroscopic methods.