6-Amino-5-cyano-1H,4H-pyrazolo[3,4-b]pyrans

The reaction of 3-methyl-1-phenyl-5-pyrazolene with arylideneamino nitriles in alcohol leads to the formation of 3-methyl-4(1-aryl-2,2-dicyanoethyl)-5-pyrazolones, which are readily cyclized in the presence of bases to the corresponding 6-amino-5-cyano-3-methyl-4-aryl- 1H,4H-pyrazolo[3,4-b]pyrans. The structures of the intermediate and final products were confirmed by the IR, UV, PMR, and mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 801–806, June, 1982.     

Nitroazines. 5. Use of the japp-klingemann reaction for the synthesis of nitrotriazines

Condensation of diazoles with -dicarbonyl nitro compounds (nitromalondialdehyde and nitromalondiester) gives derivatives of azolo[5,1-c] [1,2,4]triazine with a nitro group in the triazine ring.For 4, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 662–665, May, 1986.     

Synthesis and transformations of 3-azido-5-amino-1,2,4-triazines

The reaction of the tetrazolediazonium ion with malonic acid dinitrile and nitroacetonitrile leads to the formation of 3-azido-5-amino-1,2,4-triazine derivatives. According to the mass-spectrometric data and the results of X-ray diffraction analysis, the crystalline compounds exist in the amino form. The facile hydrolysis of the amino and azido groups to azauracils is an argument in favor of the existence of the imino form in solution.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 557–561, April, 1984.     

Effect of electron impact on 9-phenylacridines

The high intensities of the molecular-ion peaks in the mass spectra of 9-phenylacridines, the absence of ions characterizing cleavage of the interannular bond, and the high selectivity of the fragmentation constitute evidence for the presence of conjugation between the aromatic rings of the system. Dehydrogenation processes during electron impact that lead to the formation of condensed systems are peculiar to the investigated compounds. Unique detachment of an amino group from the (M-H)⁺ ion was noted for 9-(4-aminophenyl)acridines.     

Thermal heterocyclization of methyl aryl ketazines. 2. Reactions of the tautomeric enehydrazine form

Over the temperature range 220–280C the thermal reactions of methyl aryl ketazines (Ar=C₆H₅-, 4-CH₃C₆H-, 4-CH₃OC₆H₄-, and -naphthyl-) proceed with their cyclization to give pyrazoline and benzodiazepine derivatives. With an increase in temperature to 320–350C the subsequent transformations of these compounds lead to the formation of substituted pyrazoles, 1-methyl-1,2-diarylcyclopropanes isomeric olefins, low-molecular-weight aromatic hydrocarbons, and isoquinolines.See [1] for Communication 1.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 908–917, July, 1986.     

New reaction for the direct incorporation of purines in nucleophilic organic compounds

The direct incorporation of purine and theophylline residues in indole, oxindole, and pyrazolone rings was accomplished in the presence of acylating agents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 675–677, May, 1979.     

Heterocyclic derivatives of purines. 3. Synthesis and mass spectrometric study of imidazo[1,2-]purine

A mixture containing 65% 1-methyl-2-phenyl-5,7-dichloro- and 35% 1-methyl-2-phenyl-3,5,7-trichloroimidazo [1,2-f] purine (the percentages of the components were established by means of Chromatographic mass-spectrometric analysis) was obtained by refluxing 1,8-dimethyl-2-phenylimidazo [1,2-f]xanthine in POCl₃ in the presence of excess PCl₅. Reduction of this mixture with concentrated HCl in the presence of red phosphorus leads to 1-methyl-2-phenylimidazo[1,2-f] purine, while heating with piperidine gives a mixture consisting of 55% 1-methyl-2-phenyl-6-piperidino-8-chloroimidazo [1,2-f] purine and 45% 1-methyl-2-phenyl-3, 8-dichloro-6-piperidino-imidazo [1,2-f] purine. The IR, PMR, and mass spectra of the compounds obtained are discussed.See [1] for communication 2.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1125–1129, August, 1980.     

1,2-Diphenylimidazo[1,2-a]benzimidazole in electrophilic substitution reactions

Vilsmeier formylation of 1,2-diphenylimidazo[1,2-a]benzimidazole leads to the 3-formyl derivative, while heating with acetic anhydride in sulfuric acid gives the 3-acetyl derivative. The nitration of this benzimidazole with potassium nitrate in sulfuric acid gives a mixture of mono-, di-, and trinitro derivatives. Bromination in chloroform leads to a mixture containing the mono- and dibromo derivatives. The structures of the compounds obtained were confirmed by their IR, PMR, and mass spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1251–1254, September, 1981.     

Condensed imidazo-1,2,4-triazines. 23. Synthesis and reactions of 2-(1′-alkylhydrazino)-benzimidazole with acetyl(benzoyl)acetone

By reaction of 2-chlorobenzimidazole with methyl-, ethyl-, and 2-hydroxyethylhydrazine we have synthesized the corresponding 2-(1-alkylhydrazino)benzimidazoles for the first time. By refluxing the latter in alcohols with acetyl(benzoyl)acetone they form 1-(2-benzimidazolyl)-1-alkylhydrazones and, without solvent, form 1,35-trisubstituted 1,2,4-triazepino[4,3-a]benzimidazoles.For Communication 22, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1065–1068, August, 1990.     

Composition of the essential oil ofSalvia garedzhii. Terpenoids and sesquiterpene hydrocarbons

The composition of the terpenoid and sesquiterpene hydrocarbon fraction ofSalvia garedzhii has been studied by chromato-mass spectrometry. A total of 19 compounds have been identified and a provisional assignment of another 6 components has been made.K. A. Timiryazev Moscow Agricultural Academy. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 720–722, November–December, 1984.