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.     

The azo coupling of 1-aryl quaternary salts of lepidine and quinaldine and some properties of the reaction products

A series of formazans has been obtained by the coupling of 1-aryllepidinium and 1-arylquinaldinium salts with diazonium salts. The formazans have been converted by oxidation into tetrazolium salts and by the action of acids into benzotriazines. The absorption spectra in the visible region have been measured in neutral, alkaline, and acid media.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1104–1111, August, 1970.     

Studies on tellurium-containing heterocycles. Part 20. Reactions of 2-benzoselenopyrylium salts and 2-benzotelluropyrylium salts with nucleophiles: formation of 1-functionalized 1H-isoselenochromenes and 1H-isotellurochromenes

The reactions of the 2-benzoselenopyrylium (1A) and 2-benzotelluropyrylium cations (1B) with a variety of nucleophiles have been investigated. LiAlH(4), sodium alkoxide (NaOMe, NaOi-Pr and NaOt-Bu), diethylamine, n-butylamine and acetone reacted with 1 to give the 1H-isochromenes (2) and the corresponding 1-substituted products (4-9) under mild conditions in almost good to high yields. The 1-alkyl(phenyl)isoselenochromenes (10-13) and 1-benzylisochromenes (18A, 18B), which were produced by the reaction of the salts 1 with Grignard reagents, were converted to the corresponding 1,3-disubstituted 2-benzopyrylium salts (14-17, 19) by treatment with triphenylcarbenium tetrafluoroborate (Ph(3)C(+) BF(4)(-)), respectively. The 1-benzylselenopyrylium salts (19A) and 1-benzyltelluropyrylium salts (19B) exist in the solvent as an equilibrium mixture of the salts (19) and the corresponding (Z)-benzylidene compounds (20).     

Energetic polymer salts from 1‐vinyl‐1,2,4‐triazole derivatives

Energetic polymers salts from 1‐vinyl‐1,2,4‐triazole derivatives have been synthesized via free radical polymerization of 1‐vinyl‐1,2,4‐triazolium monomer salts or by protonation of poly(1‐vinyl‐1,2,4‐triazole) with inorganic or organic acids. Standard enthalpies of formation of the new monomer salts were calculated using the computationally feasible DFT(B3LYP) and MP2 methods in conjunction with an empirical approach based on densities of salts. Compared with the monomer salts, the polymer salts have good thermal properties with high densities > 1.5 g cm^?3. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2414–2421, 2008     

1-Amino-1-hydrazino-2,2-dinitroethene and corresponding salts: synthesis, characterization, and thermolysis studies

Synthesis, characterization, and thermolysis studies of 1-amino-1-hydrazino-2,2-dinitroethene (2) and salts thereof are reported. These compounds have been fully characterized by IR and NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC), density, and impact sensitivity measurements. Compound 2 decomposes at 124.5 °C (DSC) and the salts decompose over the range 138.6-181.6 °C, thus showing higher thermostability. The calculated detonation pressures (P) for these salts range from 27.2 to 37.8 GPa, and detonation velocities (vD) fall between 8424 to 9482 m s(-1); these properties make them competitive energetic materials.     

Micromodulation of electron-transfer rates in mixed-valence 1′,1″′-dibenzylbiferrocenium cations

X-Ray structures of 1′,1′″-disubstituted biferrocenium triiodide salts have been studied and the dramatic effects of substituents on the intramolecular electron-transfer rates are described.     

7-Dialkylamino-1-alkylquinolinium salts: highly versatile and stable fluorescent probes

7-Dialkylamino- and 7-alkylsulfenyl-1-alkylquinolinium salts have been synthesized using a novel synthetic approach. The key intermediate, 7-fluoro-1-methylquinolinium iodide, was shown to possess high reactivity toward nitrogen and sulfur nucleophiles, and the kinetics of this nucleophilic aromatic substitution reaction was investigated. A wide variety of compounds were synthesized and characterized spectroscopically. High fluorescence quantum yields were observed, and this was attributed to the rigid molecular architecture. The thermal and photochemical stability of a number of compounds was investigated, and it was demonstrated that 7-dialkylamino-1-methylquinolinium salts have superior stability compared to a number of hemicyanine dyes and rigid charge-transfer probes. Based on the high quantum yields, the large Stokes shifts, and in particular, the high thermal and photochemical stability, it is concluded that 7-dialkylamino-1-methylquinolinium salts are excellent color-shifting, mobility-sensitive fluorescent probes for polymer characterization and other demanding applications.     

Synthesis and Reactivity of 1-Alkyl-4-carbamoyl Dihydropyridines

The synthesis and the reactivity of dihydropyridine systems have long been investigated by our group. In particular, the preparation of dihydropyridines by borohydride reduction of 2-, 3-, 4-cyano- and 3-me- thylpyridinium salts² and by electrochemical reduction of 3-acetyl- and 3-carbamoylpyridinium salts were studied. We wish now to report the results of the reduction of 1-alkyl-4-carbamoylpyridinium salts.     

某些1-酰基苯并咪唑及1-酰基咪唑衍生物的合成

2-取代的苯氧甲基苯并咪唑、咪唑分别与酰氯在缚酸剂存在下反应,制备了24个新的1-酰基2-苯氧甲基苯并咪唑及1-苯氧乙酰咪唑衍生物.后者容易吸水,转变成相应的铵盐.所制得的化合物中某些经小麦垂直生长法测定表现出一定的促进或抑制生长活性.     

Étude voltamétrique des sels de styryl-2 et styryl-4 pyrylium. 1re partie

Voltammetric study of styryl-2 and styryl-4 pyrylium salts. Part 1. The redox properties of diphenyl-2,6 styryl-4 and diphenyl-4,6 stryl-2 pyrylium salts have been studied by means of cyclic voltammetry. These salts disclose irreversible reduction and oxidation steps that are characterised by one reduction peak and two oxidation peaks, respectively. The second oxidation peak vanishes when the switching potential is −0.75 V. The influence of water on the electrochemical behaviour of these salts as well as their degradation over several months has been studied.     

A Novel Synthesis of 1-Aminoalkanephosphonic Acid Derivatives from 1-(N-Acylamino)- alkyltriphenylphosphonium Salts

Efficient and convenient procedures for the α-amidoalkylation of trialkylphosphites with 1-(N-acylamino)alkyltriphenylphosphonium salts followed by a Michaelis–Arbuzov-type reaction to afford 1-(N-acylamino)alkanephosphonic acid esters have been developed. High yields and simple isolation and purification protocols are the main advantages of this method.     

Selective synthesis of 1,3-dialkyl-4-nitro-1,2,3-triazolium salts from 1-alkyl-4-nitro-1,2,3-triazoles and dialkyl sulfates

The process of alkylation of 1-alkyl-substituted 4-nitro-1,2,3-triazoles with dimethyl and diethyl sulfates has been studied. The structures of the N,N’-dialkyl-C-nitro-1,2,3-triazolium alkylsulfates and perchlorates has been confirmed by IR, ¹H and ¹³C NMR spectroscopy. Alkylation with an excess of dialkyl sulfate occurred regioselectively at N-3 with the formation of 1,3-dialkyl-4-nitro-1,2,3-triazolium salts, which is in agreement quantum-chemical calculations of the relative stability of the corresponding isomeric cations. The molecular and crystal structures of the first example of this type of salt – 1,3-diethyl-4-nitro-1,2,3-triazolium perchlorate – have been determined by X-ray crystallo-graphy. Nitrotriazolium salts with mixed alkyl substituents – 3-ethyl-1-methyl- and 1-ethyl-3-methyl-4-nitro-1,2,3-triazolium salts – have been synthesized an studied for the first time.     

A Facile Synthesis of 3-(21Hydroxybenzoyl)-1-Methyl-2(1H)-Pyridinones From Benzopyrano [2,3-b] Pyridines

The methyl iodide salts of benzopyrano[2,3-b]pyridines have been ring-opened to give 3-(2¹-hydroxybenzoyl)-1-methyl-2(1H)-pyridinones in high yield.     

Novel nucleophilic rearrangement of 1-substituted isoquinolines using an alcoholic sodium hydroxide solution

The reactions of 1-substituted isoquinolinium salts have been studied in the cases of the 1-isopropyl-2-methyl- and 2-methyl-1-cyclohexylisoquinolinium iodides using an alcoholic solution of sodium hydroxide. The possibility of preparing a wide range of spirocyclic ketones, alcohols, amino alcohols, and isochroman-3-ones has been demonstrated.     

Interaction of Dowex A-1 chelating resin with sparingly soluble calcium salts

The interaction between Dowex A-1 and sparingly soluble salts obeys the mass action law if no other salts are present in the solution. Increasing the total amount of charged species in the solution causes a decrease in the distribution coefficients of calcium, the decrease being in accordance with a simple function of the concentrations of the sodium ion and the precipitating anion in solution. The relations between the adsorbability and the solubility products have also been derived.     

Synthesis of novel methoxy and hydroxy derivatives of 2-phenyl-1H-benz[g]indoles

The synthesis of novel methoxy-derivatives of 2-phenyl-1H-benz[g]indole 3 by condensation of α-naphthyl-amines 1 with N-phenacyl-pyridinium salts 2 is described, as well as their conversion into the corresponding hydroxy-derivatives 5 . Unexpected quinoxaline derivatives 4 were obtained when in the condensation reaction the N-nitrophenacylpyridinium salts 2d,e have been used.     

6-(2-furyl)imidazolo[2, 1-b]thiazole and its derivatives

Imidazolo[2, 1-b]thiazoles have been obtained by cyclizing thiazolium salts synthesized by the reaction of 2-aminothiazole and 2-amino-4-methylthiazole with 2-haloacetylfurans.     

Synthesis and configurational assignment of optically active 1-hydroxyindolizidines

The four diastereomers of 1-hydroxyindolizidine have been prepared in high optical purity (>98%) by NaBH₄ reduction of the (+) and (-) 3-bromocamphor-8-sulfonic acid salts of 1-oxoindolizidine followed by separation of the resulting diastereomeric alcohols by ion-exchange chromatography.     

Synthesis of 3-Methyleneisoindolin-1-ones and Isoquinolinium Salts via Exo and Endo Selective Cyclization of 2-(1-Alkynyl)benzaldimines

Coinage metal-promoted 5-exo and 6-endo selective cyclization of 2-(1-alkynyl)benzaldimines has been studied. It was found that, under gold catalysis, 2-(1-alkynyl)benzaldimines exclusively underwent 5-exo-dig cyclization processes, followed by oxidation to form N-aryl 3-methyleneisoindolin-1-ones. In contrast, in the presence of base and under activation of AgOTf, switching of 5-exo to 6-endo cyclizations of 2-(1-alkynyl)benzaldimines was observed, exclusively giving N-aryl or N-alkyl substituted isoquinolinium salts. The two key reaction intermediates, exocyclic vinyl-Au and the endocyclic vinyl-Ag species have been isolated and characterized, and a study of their reactivities confirms the plausible mechanisms. Reactions of the resultant 3-methyleneisoindolin-1-ones with benzyne afforded structurally important isoindolinone-based benzocyclobutenes. Additionally, several interesting transformations of the resultant isoquinolinium salts have been investigated.     

Chiral pyridinium-based ionic liquids containing the (1R,2S,5R)-(−)-menthyl group

A novel class of chiral pyridinium salts in which the chirality resides in the cation have been prepared and characterized. The physicochemical and anti-microbial properties have been determined. The group of prepared salts contained chiral ionic liquids and decomposable chiral pyridinium chlorides.