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.     

Synthesis of benzimidazole derivatives

New bases and quaternary salts — 2-methylbenzimidazole derivatives — containing 2-pyridyl residues as a substituent in various positions of the benzimidazole ring were synthesized. Benzimidazolium salts of a new type with hetaryl groups attached to both nitrogen atoms were obtained. Imidacyanines were synthesized from the quaternary salts of pyridyl-substituted 2-methylbenzimidazoles, and the chief light-absorption maxima of these dyes were determined.See [1] for communication IVTranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 687–690, May, 1972.     

Synthesis of indoles from pyridinium salts 5. Secondary amines in the reaction of 3-nitropyridinium salts with acetone

The use of secondary amines in the reaction of 3-nitropyridinium salts with acetone makes it possible to isolate stable intermediates in the formation of indoles — (o-N,N-dialkylaminobenzyl)ketones — and to observe new reaction pathways — the formation of bisindolylpropanes and p-nitroanilines.See [1] for Communication 4.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1213–1221, September, 1988.     

Condensed heterocycles with a thiazole nucleus. 8. Thiazolo[4,3-a]pyrimido[5,4-e]pyrimidines

Condensation of 4-amino-2-methylthiothiazolium salts with 2,4,6-trichloro-5-formylpyrimidine or 3-R-2,4-dioxo-6-chloro-5-formyl-1,2,3,4-tetrahydropyrimidines yielded mesoionic derivatives of a new heterocyclic system — thiazolo[3,4-a]pyrimido[5,4-e]-pyrimidine — which can be used for the synthesis of polymethine dyes. The absorption maxima of these dyes are bathochromically shifted by 10–20 nm relative to the maxima of the thiazolopyrimidine analogs. The structure of the compounds synthesized was demonstrated by the PMR and IR spectra.For communication 7, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1126–1128, August, 1984.     

Synthesis,electronic structure,and physicochemical characteristics of pyrazolo[1,2-a]pyridazinium

The interaction of 1-methallylpyrazoles with acetic or propionic anhydride in the presence of perchloric acid forms products of acylation at the double bond and subsequent heterocyclization — pyrazolo[1,2-a]pyridazinium salts — that are representatives of a new heteroaromatic system. Analogous cyclization is observed in the acylation of 3-(2-hydroxy-2-methylpropyl-pyrazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1623–1631, December, 1990.     

Conversion of pyrrolo[1,2-α]pyrazinium salts to 8-aminoindolizines

The recyclization of pyrrolo[1,2-a]pyrazinium salts under the influence of a base leads to 8-aminoindolizine derivatives and is a new method for the synthesis of indolizines, as well as the first example of the Kost—Sagitullin rearrangement in the pyrazine series.See [1] for our preliminary communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 763–766, June, 1991.     

Synthesis of derivatives of 5-amino-7-oxo(6h)-1,3-dithiolo[4,5-d]pyrimidine on the basis of 2-amino-(1h,5h)pyrimidine-4,6-dione

The betaine of 2-amino-5-phenyliodonio(1H,5H)pyrimidine-4,6-dione, upon interaction with sodium diethyldithiocarbamate, forms the previously unknown 2-amino-5-diethylaminothiocarbonylthio (1H,5H)pyrimidine-4,6-dione, the cyclization of which in concentrated sulfuric acid leads to salts of 2-diethylimmonio-5-amino(6H)-1,3-dithiolo[4,5-d]pyrimidin-7-one — a new heterocyclic system. The salts serve as the starting material for obtaining 5-amino-7-oxo(6H)-1,3-dithiolo[4,5-d]pyrimidine-2-selenone and -2-thione.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1117–1121, August, 1992.     

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].     

Synthesis of condensed derivatives of indolo[2,3-c]pyrylium salts and β-carbolines

Tetra- and pentacyclic indole [2,3-c] pyrylium salts were obtained by acylation of 2-(3-indolyl) dimedone and 2- (1-ethyl-3-indolyl)indan-1,3-dione. The latter salts by the action of ammonia are converted to the corresponding -carbolines — derivatives of the natural alkaloid harman.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 363–366, March, 1985.     

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.     

Photochemical Cleavage of the N—O Bond in 1-Benzoyloxy-4-[4-(dimethylamino)styryl]pyridinium Salts

The effect of UV or visible light on solutions of 1-benzoyloxy-4-[4-(dimethylamino)styryl]pyridinium salts in acetonitrile solution lead to cleavage of the N—O bond and formation of 4-[4-(dimethylamino)styryl]pyridine.     

Synthesis of 2-methylthie no [3,2-b]thieno-[2,3-d]thiazole

A new heterocyclic base — 2-methylthieno[3,2-b]thieno[2,3-d]thiazole — was synthesized by heating 2-acetamido-3-hydroxythieno[3,2-b]thiophene with phosphorus pentasulfide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1039–1041, August, 1976.     

Synthesis of indoles from pyridinium salts. 6. Reaction of 3-nitroquinolinium salts with ketones in the presence of amines

It is shown that in the reaction of 3-nitroquinolinium salts with aliphatic ketones and amines the ketone adds to the 2 and 4 positions with the formation of tricyclic adducts — benzazabicyclononane derivatives. Their conformational analysis was carried out on the basis of the NMR spectral data. Intermediate products of the monoaddition of ketones in the 4 position of the heteroring were isolated for the unsubstituted 3-nitroquinolinium salt.See [1] for Communication 5.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1385–1393, October, 1988.     

Mass spectrometry and structure of ions of heterocyclic compounds activated by collision: Naphthiridines and benzazines

The dissociation and the structure at the isomeric [M — HCN]⁺ and [M — 2HCN]⁺ ions, formed during the fragmentation of naphthiridines and benzazines, were investigated by the collisionally activated dissociation (CAD) method. It was established that the stable [M — HCN]⁺ ions of 1,5- and 1,8-naphthiridines, 1,6-naphthiridine, quinoxaline, and quinazoline have different structures. The [M — 2HCN]⁺ ions can exist in two isomeric forms, one of which is characteristic of naphthiridines and the other of benzazines.Translated from Teoreticheskaya i Éksperimental'naya Khimiya, Vo. 25, No. 5, pp. 626–629, September–October, 1989.     

Investigations in the field of perinone compounds

The directed synthesis of structurally isomeric nitronaphthaloperinones — 10-nitro-and 11-nitro-14H-benz[4,5]isoquinolino[2,1-a]perinidin-14-ones — has been effected.For Communication I, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 6, pp. 842–843, June, 1970.     

Selenonaphtheno[2,3-d]thiazole derivatives as polymethine dyes

New polymethine dyes — selenonaphtheno[2,3-d]thiazole derivatives — were synthesized. It is shown that all of the synthesized dyes which have a selenonaphtheno[2,3-d]thiazole residue are more deeply colored than the corresponding 6,7-benzobenzothiazole and thionaphtheno[2,3-d] thiazole derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 459–461, April, 1971.     

Synthesen in der Pyridazin-Reihe, 26. Mitt.:

Zusammenfassung Es wird über die Synthese von verschiedenen methylsubstituiertens-Triazolo[4,3—b]pyridazinen berichtet. Außerdem wurdens-Triazolo[4,3—b]pyridazin und seine 7-Methyl- und 6-Chlor-Derivate der homolytischen Methylierung unterworfen, die Reaktionsgemische gaschromatographisch auf einzelne Methyl-s-triazolo[4,3—b]pyridazine aufgetrennt und die Verbindungen identifiziert.

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Syntheses of pyridazines, XXVI: Synthesis and homolytic methylation of s-triazolo[4.3—b]pyridazines

The syntheses of some methyl substituteds-triazolo[4,3—b]-pyridazines are reported.s-Triazolo[4.3—b]pyridazine and its 7-methyl and 6-chloro analogs were submitted to homolytic methylations and the obtained reaction mixtures were separated by gas chromatography into particular components which were then identified.

     

Synthesis of new condensed heterocyclic systems

Two new diamines — [1,3-bis(5-phenyl-1,2,4-triazol-3-yl)-4,6-diamino]benzene and [1,3-di-(2-benzimldazolyl)-4,6-diamino]benzene — were synthesized from 4,6-dinitroisophthalic acid. Newheterocyclic systems — 3,5,9,11-tetraphenyl[benzo[1,2-a; 4,5-a]bis(1,2,4-triazolo[4,3-c]pyrimidine)] and 2,16-diphenyl[benzo[1,2-a;4,5-a']bis(pyrimido[1,6-a]benzimidazole)]—were obtained by reaction of the diamines with benzoyl chloride and subsequent cyclization.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1274–1277, September, 1977.     

Imidazo[1,2-α]quinoxaline and its transformations

7-Substituted imidazo [1,2-a]quinoxalines were synthesized. Transformations of compounds of this series — quaternization, reduction to 4,5-dihydro derivatives, and behavior toward oxidizing agents — were studied.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1558–1560, November, 1972.     

Analogs of oxytocin with L- and D-pentafluorophenylalanines in the second position

Summary 1. The separation of pentafluorophenylalanine into optical antipodes has been effected.2. Two new analogs of oxytocin — [2-L-pentafluorophenylalanine]oxytocin and [2-D-pentafluorophenylalanine]oxytocin — have been synthesized and their uterotonic activities have been studied.3. It has been shown that donor — acceptor interaction plays a fundamental role in the stimulation of the biological effect.A. A. Zhdanov Leningrad State University. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 392–398, May–June, 1977.