Stable 1,2,4-triazolo[1,5-a]-pyrimidinium salts

2,3-Diamino-5,7-diaryl-1,2,4-triazolo[1,5-a]pyrimidinium salts have been synthesized by the cyclocondensation of 3,4,5-triamino-1,2,4-triazole with 1,3-diaryl-2,3-propanes, and their structures and chemical properties have been studied.Kharkov State University, Kharkov 310077, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 796–804 June, 1999.     

Synthesis and in vitro cytotoxic evaluation of new derivatives of pyrido[1,2-a]benzimidazolic ring system: the pyrido[1',2':1,2]imidazo[4,5-h]quinazolines

Access to the original series of pyrido[1',2':1,2]imidazo[4,5-h]quinazoline was developed from a 1,3-dicarbonyl unit with some "N-C-N" bisnucleophilic reagents and the derivatives obtained were evaluated for in vitro cytotoxic activities against HL60 and A2780 cells. All compounds exhibited cytotoxic activities on resistant cell lines (MDR+; HL60R and A2780R) with no resistance phenomena.     

New polyazaheterocycles. 9-Methyl-di-s-triazolo[4,3-a:4,3-c]pyrimidine and 9-methyl-s-triazolo[4,3-c]tetrazolo[1,5-a]pyrimidine

9-Methyl-di-s-triazolo[4,3-a:4,3-c]pyrimidine and 9-methyl-s-triazolo[4,3-c]tetrazolo[1,5-a]pyrimidine have been synthetized from 4-hydrazino-7-methyl-s-triazolo[4,3-c]pyrimidine. Structural assignments based on nmr, ir and chemical manipulations are discussed.     

2-Pyridylnitrene from tetrazolo[1,5-a]pyridine and pyrido[2,3-a][1,2,4]oxadiazol-2-one

Flash vacuum thermolyses of tetrazolo[1,5- a]pyridine and pyrido[2,3- a][1,2,4]oxadiazol-2-one generate 2-pyridylnitrene, which was detected by Ar matrix ESR spectroscopy. The thermolysis products are 2-aminopyridine, Z- and E-glutacononitriles, and 2- and 3-cyanopyrroles. The products are formed in the same ratios from the two precursors.     

咪唑[1,5-a]吡啶型离子液体的合成及分子识别性能

以联苯胺为原料,通过三组份串联反应一步合成咪唑[1,5-a]吡啶型离子(L),其结构经1H NMR,13C NMR,IR和X-射线单晶衍射表征。利用荧光光谱研究了L在乙腈中对对苯二甲酸(A1)、4,4'-联吡啶(A2)、吡啶(A3)、丙二酸(A4)、1,8-二氨基萘(A5)等分子的识别性能。结果表明,L对对苯二甲酸具有选择识别性能。     

Reactivity of 7-(2-dimethylaminovinyl)pyrazolo[1,5-a]pyrimidines: Synthesis of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidine derivatives as potential benzodiazepine receptor ligands. 1

A series of 7-methylpyrazolo[1,5-a]pyrimidines were reacted with dimethylformamide dimethylacetal to give the corresponding dimethylaminovinyl derivatives. These were reacted with ammonium acetate affording, through a ring closure, a number of 6-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidines bearing various substituents on the pyrazole ring. The 6-acetyl-2-hydroxy-7-methylpyrazolo[1,5-a]pyrimidine was used as starting material for obtaining some O-alkyl derivatives. Catalytic transfer hydrogenation of 2-benzyloxy-6-methylpyrazolo[1,5-a]pyrido[3,4-e]pyrimidine led to the 2-hydroxy derivative.     

Synthesis of pyrido[1,2-a]benzimidazoles from 2-acylmethyl-1H-benzimidazoles

Methods are proposed for the synthesis of previously unknown pyrido[1,2-a]benzimidazoles via the cyclocondensation of 2-acylmethyl-1H-benzimidazoles with malononitrile, triethylorthoformate ester, or ethoxymethylenemalononitrile. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1073–1079, July, 2006.     

Reactivity of 7-(2-dimethylaminovinyl)pyrazolo[1,5-a]pyrimidines: Synthesis of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidine derivatives as potential benzodiazepine receptor ligands. 2

A series of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones was obtained by reaction of ammonium acetate with ethyl 7-dimethylaminovinylpyrazolo[1,5-a]pyrimidine-6-carboxylates and these had been prepared from ethyl 7-methylpyrazolo[1,5-a]pyrimidine-6-carboxylates by reaction with dimethylformamide dimethylacetal. Under these conditions the compounds bearing a 2-hydroxy group were also O-alkylated. During the preparation of the ethyl 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylate the corresponding 5-methyl isomer was isolated and identified.     

Dipyrrolo[1,2-a:2',1'-c]pyrazines. 8. Electrophilic Substitution in Dipyrrolo[1,2-a:2',1'-c]pyrazines and 5,6-Dihydrodipyrrolo[1,2-a:2',1'-c]pyrazines. Acylation of Dipyrrolo[1,2-a:2',1'-c]pyrazines

Esters, nitriles, and amides of dipyrrolo[1,2-a:2',1'-c]pyrazines have been synthesized by the acylation of dipyrrolo[1,2-a:2',1'-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a:2',1'-c]pyrazines with trichloroacetic acid chloride, p-tosyl isocyanate, and isocyanatophosphoric acid dichloride (Kirsanov isocyanate).     

Pyrido[1',2':1,5]pyrazolo[4,3-b]quinolines as New Fluorescent Heterocyclic Systems for Dye-Sensitized Solar Cells

Russian Journal of General Chemistry - New fluorescent heterocyclic compounds pyrido[1',2':1,5]pyrazolo[4,3-b]quinolines have been synthesized by the reaction of...     

Synthesis of Substituted 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines

A one-pot synthetic approach to the novel 5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepines by thermal cyclization of 4-acylhydrazino-2,3-dihydro-1H-1,5-benzodiazepines is described.     

Chemical reactivity of [1,2,3]triazolo[1,5-a]- and [1,5-c]-pyrimidinium salts

The chemical reactivity of the [1,2,3]triazolo[1,5-a]- and [1,5-c]-pyrimidinium salts towards morpholine, water and sodium methoxide have been studied. Among others, new 1-aza and 2-azabutadienes substituted by a [1,2,3]-triazole ring were obtained in the course of the opening of the positively charged pyrimidine ring.     

Synthesis of thiopyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidines

<正>Reactions of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative 1 withα-halo-carbonyl compounds gave the ortho-substituted intermediates 2a-c which were converted into furo[2,3-b]thiopyrano[4,3-d]pyridines 3a-c by fusion of a furan moiety under basic conditions.Further cyclization of 3a-c led to a fusion of a pyrimidine ring,yielding the tetracyclic products 6,7 and 8.In addition,condensation of 6 with various aromatic aldehydes afforded the corresponding imines 9a,b.Mannich reaction of 7 gave products 10a,b.     

Synthesis of triazolo[4,3-d], tetrazolo[1,5-a] -and quinazolino[3,2-d] [1,4] benzodiazepines

Treatment of 5-methylmercapto-1,4-benzodiazepine (I) with hydrazine hydrate gave the 5-hydrazino derivative (II, R = H) which, in turn, was conveniently cyclized to the title compounds. Another method for the synthesis of triazolo [4,3-d] [1,4] benzodiazepines (III) is also described.     

sym-Triazolo[4,3-a][1,3]diazacycloalkanes. 4. Synthesis and transformations of 2-aminothiocarbonyl-sym-triazolo[4,3-a]pyrimidine

In the reaction of 1-ethoxycarbonyl-2-methylthio-1,4,5,6-tetrahydropyrimidine with thiosemicarbazide, 2-aminothiocarbonyl-3-oxo-2,3,5,6,7,8-hexahydro-sym-triazolo[4,3-a]pyrimidine is formed, which as a result of the successive action of methyl iodide, K₂CO₃ solution, and cyclic amines, converts into 2,3,5,6,7,8-hexahydro-8-oxo-sym-triazolo[4,3-a]pyrimidine.For Communication 3, see [1]Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1540–1542, November, 1987.     

Research on nitrogen containing heterocyclic compounds. XIX: Synthesis of 8H-imidazo[2,1-c]-s-triazolo[4,3-a]-[1,4]benzodiazepine and its 1-derivatives

Reaction of 2-nitrobenzyl iodide with 1H-imidazole, in the presence of potassium tert-butoxide and 18-crown-6, gave 1-(2-nitrobenzyl)-1H-imidazole. Trichloroacetylation of this compound furnished trichloroacet-ylimidazole 8 , which on treatment with sodium ethoxide was transformed into the corresponding ethoxycarbonyl derivative 9 . Catalytic reduction of the nitro group to the amino group yielded 10 , which was then cyclized to 10,11-dihydro-11-oxo-5H-imidazo[2,1-c][1,4]benzodiazepine 11. Treatment of this lactam with di-4-morpholinylphosphinic chloride followed by reaction of the intermediate 12 with formylhydrazine gave the title compound or its 1-derivatives when acetylhydrazine or isonicotinoylhydrazine were used instead of formylhydrazine.