Polymethine dyes — Furo[3,2-f]quinol-7-yl and furo[3,2-f]quinol-9-yl derivatives

New heterocyclic bases — 7- and 9-methylfuro[3,2-f]quinolines — were synthesized by condensation of 5-aminobenzofuran double tin hydrochloride salt with paraldehyde in dilute hydrochloric acid and with methyl vinyl ketone in ethanol in the presence of ferric chloride and zinc chloride. Polymethine dyes of various types were obtained from the quaternary salts of the synthesized bases. The introduction of a furan ring in the 5,6 position of quino-2- and quino-4-carbocyanines gives rise to a smaller bathochromic effect than the analogous introduction of a thieno and, particularly, a benzo group.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 391–394, March, 1977.     

Synthesis and investigation of merocyanine dyes

New merocyanine dyes — derivatives of 1-unsubstituted, 1-methyl-, and l-phenyl-3,4-pyrroline-2,5-diones — were synthesized by the reaction of quaternary salts of 2-methyl — substituted heterocyclic nitrogen bases with the appropriate 3,4-dihalopyrrolinedione and sodium benzenesulfinate or with 3-phenylamlno-4-phenylsulfonylpyrroline-2,5-diones.The effect of substituants attached to the nitrogen atom of 3,4-dihalo-3,4-pyrroline-2,5-diones on the nature of the products formed by reaction with aniline and sodium benzene-sulfinate was investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1387–1390, October, 1971.     

Cyanine dyes from seven-membered heterocyclic systems

The condensation of o-aminothiophenol with tetrahydroacetophenone, 2-ethylidenecyclohexanone, and 2-benzylidenecyclohexanone and also the condensation of N-methyl-o-aminothiophenol with 2-benzylidenecyclohexanone has given the bases of derivatives of benzo[b]cyclohexano[f]- and -[e]-1,4-thiazepines. From the hydrochlorides, perchlorates, and quaternary salts of these bases, cyanine dyes have been synthesized. The dyes—norcyanines—exhibit solvatochromism, which is explained by the existence of a hydrogen bond between the molecules of the dye and an alcohol.For part IV, see [3].     

Structures and reactivities of benzo-1,2,3-dithiazolium salts and their selenium analogs

A number of benzo-1,2,3-dithiazolium chlorides (I) and their selenium analogs — benzo-1,2,3-thiaselenazolium, benzo-2,1,3-thiaselenazolium, and benzo-1,2,3-diselenazolium salts — were synthesized. The electronic structures and reactivities of the I cation and salts I–IV are discussed on the basis of a quantum-chemical calculation of cation I and the PMR spectra of salts I–IV. Successive substitution of the sulfur atoms in the I cation by selenium atoms, particularly in the 2 position, substantially increases the degree of transfer of positive charge to the condensed benzene ring. The trend of the nucleophilic reactivities of 6-methoxy derivatives of salts I–IV in the reaction with aromatic amines is the same as the trend of the degree of localization of the positive charge in the 6 position.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 912–916, July, 1978.     

Quino-4-cyanines with carbonyl-containing substituents

6-Carbonyl-substituted lepidines and their quaternary salts were synthesized. Quino-4-cyanines were obtained from them. The introduction of carbonyl-containing substituents substantially deepens the color of the dyes obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 943–947, July, 1984.     

1-Ethyl- and 1,2-dimethyl-3-(p-methoxyphenyl)benzo[f]quinolines and their transformations

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.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1223–1226, September, 1976.     

Condensation of ethanolamine with chloro-sym-triazines

2,2-Aminoethoxy-sym-triazines have been synthesized by reduction of cyanomethoxy-sym-triazines or by the reaction of sodium 2-aminoethoxide with quaternary ammonium salts of sym-triazines. Their structures have been established by PMR and mass spectral examination.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 657–659, May, 1989.     

Synthesis of benzimidazole derivatives

Phenylhalides of 1-phenyl-2-methylbenzimidazole were synthesized and converted to a new type of imidacyanin dye with phenyl groups on both nitrogen atoms of the benzimidazole residue. The heretofore unknown imidadicarbocyanins were obtained from quaternary salts of 1-phenyl-2-methylbenzimidazole (or its derivatives) which contain electronegative substituents in the 5 position.See [1] for Communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1559–1561, November, 1970.     

Heterocyclic analogs of pleiadiene. 51. N-acylperimidines: Ring opening instead of deacylation under the influence of nucleophiles

N-Acetyl- and N-benzoylperimidines, as well as quaternary salts based on them, were synthesized. It is shown that the heteroring is opened to give N-acyl derivatives of 1,8-naphthalenediamine by the action of nucleophiles on N-acyl-perimidines and N-benzoylperimidine salts.See [1] for Communication 50.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1398–1403, October, 1980.     

Analogs of styryl dyes and the simplest AZO dyes from 2-dimethylaminothiophene

The condensation of 2-dimethylaminothiophene with the appropriate derivatives of quaternary benzothiazole salts has give the vinylene-homologous series of dyes with the structure (I). By coupling with benzenediazonium salts, the simplest azo dyes of structure (III) have been synthesized. The influence on the absorption spectra of the replacement of a dimethylaniline nucleus in polymethine and azo dyes by a 2-dimethylaminothiophene nucleus has been investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 923–925, July, 1973.     

1-Vinyl-4-alkyl-1,2,4-triazolium salts

Quaternary salts based on 1-vinyl-1,2,4-triazole have been synthesized. Alkyl i-odides and bromides and dimethyl sulfate served as the quaternizing agent. Polymeric quaternary salts of 1-vinyl-1,2,4-triazole have been obtained by alkylation of its polymer.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1412–1414, October, 1984.     

Reaction of 1-vinylbenzotriazole with alkyl halides and dialkyl sulfates

Adducts of alkyl halides and dialkyl sulfates with 1-vinylbenzyltriazole were synthesized, and their IR and UV spectra were investigated. The nitrogen atom in the 3 position is the coordination center in these quaternary nitrogen salts.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1571–1574, November, 1972.     

Dipyrazolinyl-substituted 1,4-distyrylbenzenes

A number of dipyrazolinyl-substituted 1,4-distyryl- and 1,4-distyryl-2-methylbenzenes — new luminophores that have intense yellow-green luminescence — were obtained by the Wittig reaction by refluxing 1-(4-formylphenyl)-3-aryl-5-phenyl-2-pyrazolines and aromatic bisphosphonium salts in isopropyl alcohol in the presence of sodium isopropoxide. The low reactivities of the aldehydes used and the predominant formation of trans isomers in the Wittig reaction are noted. Data from the IR and electronic absorption spectra and the fluorescence spectra of the synthesized compounds are presented.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 532–535, April, 1979.     

Reduction of quaternary salts of 3-azafluorene and 3-azafluorenone and their conversion to indenoindolizines

The tetrahydro and hexahydro derivatives with respect to the nitrogen-containing ring were obtained by reduction of 3-azafluorene and 3-azafluorenone methiodides, respectively, with sodium borohydride. Indenoindolizines with linear and angular structures were synthesized from the N-phenacyl quaternary salts of 3-azafluorenones via 1,3-dipolar cycloaddition and by the Chichibabin method. 7-Nitro-3-azafluorenone and 3-azafluorenone N-oxide were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 252–255, February, 1983.     

Secondary ion mass spectra of organic cationic dyestuffs

Rules for the behavior under fast atom bombardment (FAB) have been established for 15 cationic dyes — quaternary ammonium salts of heterocyclic amines and heterocycles containing quaternary nitrogen atoms with aliphatic substituents. Intense peaks corresponding to the molecular mass of the cationic part of the dyes [M-Hal]⁺ are observed in the spectra of all the derivatives. Fragmentation of the azodyes is determined by the azo group and the heterocyle. The base peaks in the case of compounds containing a quaternary nitrogen atom with aliphatic substituents correspond to the ammonium ion and a fragment of amine type. The results obtained can be used to identify dyes of unknown structure from their secondary ion mass spectra (SIMS).DeceasedTranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1411–1417, October, 1992     

Modification of the sesquiterpene lactone arteannuin B and antimicrobial activities of the products obtained

A number of amino derivatives have been synthesized from the sesquiterpene lactone arteannuin B, and quaternary salts have been obtained from them with alkyl halides. The results are given of a study of the antimicrobial activities of the modified derivatives.Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 714–717, September–October, 1997.     

Polyfuryl(aryl)alkanes and their derivatives. 8. Synthesis of benzofuro[2,3-h]-1-oxaazulenium salts. molecular and crystal structures of 2,4-dimethylbenzo[b]furo[2,3-h]-1-oxaazulenium perchlorate

The first representatives of a new heterocyclic system — benzofuro[2,3-h]-1-oxaazulenium salts — were synthesized. Diverse variations of the synthesis of these compounds are proposed. The molecular and crystal structures of 2,4-dimethylbenzo[b]furo[2,3-h]-1-oxaazulenium perchlorate were studied.See [1] for our preceding communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 627–632, May, 1993.     

Quaternary salts of quinolybenzimidazoles

The nitrogen atoms of the benzimidazole ring are alkylated initially in the quaternization of 2-(2-quinolyl)benzimidazole, and the nitrogen atom of the quinoline ring is alkylated only after this. Pyridyl- and quinolylbenzimidazoles and their quaternary salts were synthesized in order to study geometrical isomerism in the dihetaryl series. It was concluded that geometrical isomerism cannot occur in the case of the protonated forms or any other quaternary salts of dihetaryls, since as a result of the mutual electron-acceptor effect of the heteroaromatic cations the carbon-carbon bond between them is converted to a single bond, despite the fact that it is a bond between two sp² carbon atoms.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1662–1669, December, 1980.     

Thermolysis of quaternary salts of 2-methylbenzothiazole and their methylene bases

The pathways of the thermal transformations of quaternary salts of 2-methylbenzothiazole and their methylene bases were investigated. The schemes of the thermal fragmentation of these compounds are discussed. The possibility of the formation of methylene bases in the thermolysis of quaternary salts of 2-methylbenzothiazole is demonstrated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1620–1625, December, 1981.     

2-Benzopyrylium salts

The synthesis of berberine analogs — substituted dibenzo[a,g]quinolizinium salts — was worked out on the basis of 2-benzopyrylium salts.See [1] for communication XXII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1481–1483, November, 1977.