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.     

Synthesis and structure of O-(arylcarbamoyl)butyrhydroximoyl chlorides

The O-(arylcarbamoyl)butyrhydroximoyl chlorides were synthesized, and the x-ray structural analysis (XSA) of one of them — O-(o-tolylcarbamoyl)butyrhydroximoyl chloride — was performed. It was established from the data of the XSA and the PMR spectra that all synthesized compounds are the Z isomers.Institute of Physiologically Active Substances, Russian Academy of Sciences, 142432 Chernogolovka. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 2, pp. 315–319, February, 1992.     

Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone,flavone, and isoflavone

Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan — silibin — have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed.For article 10, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–198, February, 1986.     

Sulfonamides as ionophores for ion-selective electrodes. IV. New secondary sulfonamide podands and cryptands

New compounds — podands and cryptands with two secondary sulfonamide groups —have been synthesized and are described. They were tested as ionophores for guanidinium ions in PVC-membrane electrodes with bis (2-ethylhexyl)sebacate (DOS) as plasticizer.     

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.     

Investigation of 2,6-dichlorojulolidines and 1-aryl-2,5-di(chloromethyl)pyrrolidines

9-Substituted 2,6-dichlorojulolidines and 1-aryl-2,5-di(chloromethyl)pyrrolidines-alkylating compounds with alkylating centers in fixed positions — were synthesized, and their basicities and rates of hydrolysis were determined. The relationship between the structure, basicity, and rate of hydrolysis of these compounds is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 41–44, January, 1972.     

Synthesis and spectroscopic properties of soluble aza analogs of phthalocyanine and naphthalocyanine

The syntheses of aryl-substituted octaaza analogs of phthalocyanine — tetra-2,3-(4,5-diphenylpyrazino)porphyrazin and its vanadyl complex — and also of the vanadyl complex of tetra-2,3-(4-phenylquinolino)porphyrazin — a tetraaza analog of naphthalocyanine — are described. A modified singlestage method for the synthesis of the previously reported tetra-2,3-(5-tert-butylpyrazino)porphyrazin is put forward. The electronic absorption spectra of the compounds synthesized have been studied in organic solvents and acid media — in sulfuric acid solution and in organic solvents with the addition of phenol or trichloroacetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 58–63, January, 1993.     

Mechanism of the nucleophilic substitution of hydrogen in azines III. Intermediates in the aminoarylation of 2-quinoxalone

The intermediates in the replacement of hydrogen in 2-quinoxalone by arylamines were recorded by PMR spectroscopy. The synthesized model compounds — 3,4-dihydro-3-R-quinoxal-2-ones — are spectrally identical to the observed intermediates. Under the reaction conditions they undergo reversible decomposition to the starting compounds and are oxidized to give the reaction products. 6-Nitro-2-quinoxalone forms stable addition products in the reaction with arylamines. The polarographic oxidation of 3,4-dihydro-3-R-quinoxal-2-ones and the model compounds shows that primarily the dihydro fragment of the molecule is oxidized.s singlet - d doublet - dd doublet of doublet See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 684–689, May, 1977.     

Benzindoles. 18. Some electrophilic substitution reactions involving the hydrogen atoms in 4,5,6,7-dibenzindole

The principal electrophilic substitution reactions involving the hydrogen atom of 4,5,6,7-dibenzindole — the Vilsmeier reaction, the Mannich reaction, diazo coupling, and acylation — were studied, and a qualitative comparison of its reactivities with indole and 4,5- and 6,7-benzindoles was made. It was established that 4,5,6,7-dibenzindole has the most clearly expressed electron-donor properties. The structures of the synthesized compounds were proved by data from the IR, UV, PMR, and mass spectra.See [1] for communication 17.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 366–370, March, 1979.     

Geometry and mesomorphic properties of new schiff bases containing thiazole ring

New liquid-crystalline azomethines — 2-(4-alkoxybenzylideneamino)-4-(3-nitrophenylamino)thiazoles —displaying nematic mesomorphism at 42–137°C have been synthesized. The structure of these compounds was studied by the MNDO LCAO MO method. A correlation was found between the geometric parameters and liquid crystal properties.Bashkir State University, 450074 Ufa, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1242–1248, September, 1999.     

Synthesis of some new arylindoles

New indole derivatives — 2-ethoxycarbonyl-5(p-acetylphenyl)indole andpara-substituted 2-diphenylindoles —key compounds for synthesis of new bisindoles, were synthesized from 4-acetyl-4-nitrodiphenyl.I. Dzhavakhishvili Tbilisi State University, Tbilisi 380028. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1351–1354, October, 1994. Original article submitted September 15, 1994.     

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.     

Reaction of pyridine-2-thione with acetylenes

In contrast to 2-pyridone, pyridine-2-thione reacts with acetylene with the participation of one reaction center — the sulfur atom. The reaction with phenylacetylene and diacetylene proceeds stereospecifically to give products with cis structures. The structures of the synthesized compounds were confirmed by chemical and spectroscopic methods.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 364–367, March, 1978.     

Synthesis of diquinone derivatives of deuteroporphyrin ix for the study of the first stage in the process of photosynthesis

Diquinone derivatives of deuteroporphyrin IX containing covalent bridges of different lengths between the chromophores have been synthesized. The compounds were prepared by the condensation of hydroxy-quinones with deuteroporphyrin IX using a mixed anhydride method which employed the system di-tert-butyl pyrocarbonate — 4-dimethylaminopyridine. A spectral study of the resulting porphyrin-quinones was carried out.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 176–182, February, 1992.     

Behavior of N-alkoxybenzimidzoles with respect to nucleophilic reagents. Attempts to synthesize N-hydroxy-2-aminobenzimidazoles

Various possibilities for the synthesis of N-hydroxy- and N-alkoxy derivatives of 2-aminobenzimidazoles — reductive cyclization of o-nitrophenylureas, the action of sodium amide on 1-alkoxybenzimidazoles, the ammonolysis of 1-alkoxy-2-iodobenzimidazoles, etc. — were investigated. Organometallic compounds of 1-alkoxybenzimidazoles were obtained for the first time, and their reactivities with respect to benzophenone, iodine, and 1-substituted benzimidazoles were studied. 2,2-Dibenzimidazolyls that contain an alkoxy group in the 1 position were synthesized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 200–206, February, 1979.     

Synthesis and isolation of monoesters of sucrose and arachidonic acid

Monoesters of sucrose and arachidonic acid have been synthesized by the transesterification of ethyl arachidonate with unprotected sucrose, and the structural isomers — 6-O-arachidonoylsucrose, 6-O-arachidonoylsucrose, and 3-O-arachidonoylsucrose — have been separated chromatographically. The positions of the ester bonds in these compounds were determined by the¹³C NMR method.All-Union Scientific-Research Institute of the Technology of Blood Substitutes and Hormone Preparations, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 499–502, July–August, 1988.     

Synthesis of hydroxyamines of diacetylene series

Conclusions We synthesized some previously unknown types of polyfunctionally substituted compounds of the diacetylene series by the condensation of 4-hydroxy-3-alkyl (or dialkyl)amino-1-butynes with various bromoacetylenes under the conditions of the Cadiot — Chodkiewicz reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1088–1091, May, 1971.     

Preparation and covalent hydration of 4H-imidazole derivatives

2,4,4-Trimethyl-5-phenyl-4H-imidazole, 4H-imidazole 3-oxide, and 4H-imidazole 1,3-dioxide were synthesized from 1-hydroxy-2,5,5-trimethyl-4-phenyl-3-imidazoline and 3-imidazoline 3-oxide, The action of hydrogen chloride on these compounds and on 2,4,4-trimethyl-5-phenyl-4H-imidazole 1-oxide gives products of the addition of water or alcohol — derivatives of 4-hydroxy-2-imidazolinium chlorides.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1246–1251, September, 1972.     

Synthesis of furo[2,3-f]- and furo[3,2-e]indole derivatives

Two compounds — the diethylamides of 1,2-dimethyl-3-carbethoxy-6-carboxyfuro[2,3-f]- and 1,2-dimethyl-3-carbethoxy-5-carboxvfuro[3,2-e]indoles — are formed in the reaction of 1,2-dimethyl-3-carbethoxy-5-hydroxyacetic acid (I) with dimethylformamide and phosphorus oxychloride as a result of subsequent intramolecular cyclization of the intermediates. This constitutes evidence for formylation of the starting acid in the 6 and 4 positions. Formylation of the ethyl ester of acid I gives only the 6-formyl derivative, the intramolecular cyclization of which under the influence of sodium ethoxide gives 1,2-dimethyl-3,6-dicarbethoxyfuro[2,3-f]-indole. Hydrolysis of the latter with alcoholic alkali gives the corresponding dicarboxylic acid. The structures of the synthesized compounds were confirmed by the PMR, IR, and mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 766–769, June, 1977.     

Synthesen und Reaktivität von 2,3,6,7,8-Pentachlorimidazo-[1,2—b]pyridazin und 3,6,7,8-Tetrachlor-s-triazolo-[4,3—b]pyridazin

Zusammenfassung 2,3,6,7,8-Pentachlorimidazo[1,2—b]pyridazin und 3,6,7,8-Tetrachlor-s-triazolo[4,3—b]pyridazin wurden aus unsubstituierten Verbindungen und einigen Chlor-Derivaten synthetisiert. Die Reihenfolge der Substitution von Wasserstoffatomen durch Chloratome konnte beim Imidazo[1,2—b]pyridazin als 3>2, 7>8>6 ermittelt werden, während beis-Triazolo-[4,3—b]pyridazin der Verlauf als 3>8>7>6 sichergestellt wurde. Nukleophile Substitutionen an diesen perchlorierten Systemen verlaufen am leichtesten in Stellung 8.

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Pyridazines. XLVIII: Syntheses and Reactivity of 2,3,6,7,8-Pentachloroimidazo[1,2—b]pyridazine and 3,6,7,8-Tetrachloro-s-triazolo[4,3—b]pyridazine

2,3,6,7,8-Pentachloroimidazo[1,2—b]pyridazine and 3,6,7,8-Tetrachloro-s-triazolo[4,3—b]pyridazine were synthesized from the parent compounds and some of their chloro derivatives. It could be established that in the case of the first condensed system the stepwise introduction of chlorine atoms followed the order of 3>2, 7>8>6 and in the case of the second system this appears to be 3>8>7>6. Nucleophilic substitutions on these perchloro compounds proceed most easily at position 8.