Reduction of 2,3,4-substituted quinolines with sodium borohydride

1,2-Dihydroquinolines were obtained by the reduction of 3-substituted 2-methyl-4-phenylquinolines with sodium borohydride in aliphatic carboxylic acids; N-alkyl derivatives are also formed. The corresponding 1,4-dihydroquinoline was obtained in the reaction of 2-methyl-3-nitroquinolinium perchlorate with sodium borohydride.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1680–1686, December, 1991.     

Reduction of 3-substituted 2-methylquinolines with sodium tetrahydroborate

Reduction of esters of 2-metylquinoline-3-carboxylic acids and their perchlorates gave esters of 1,4-dihydro-2-methylquinoline-3-carboxylates, while derivatives of 1,2-dihydroquinoline were formed in the case of 1,2-dimethyl-3-ethoxycarbonyl-7-methoxyquinolinium perchlorate. Reduction of esters of 2-methylquinoline-3-carboxylic acid, 1,2-dimethyl-3-ethoxycarbonyl-1-methoxyquinolinium perchlorate and 3-acetyl-2-methyl-quinoline with sodium tetrahydroborate in acetic acid gave esters of 1,2-dimethyl- and 2-methyl-1,2,3,4-tetrahydroquinoline-3-carboxylic acid and 3-acetyl-2-methyl-1,2,3,4-tetrahydroquinoline.Latvian Institute of Organic Synthesis, Riga, LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1383–1390, October, 1996. Original article submitted October 11, 1995.     

Equilibrium NH-acidity of 1,4-dihydropyridines and 4,5-dihydroindeno[1,2-b]pyridines

The patterns governing the dependence of NH-acidity on the presence of -, - and -substituents in the 1,4-dihydropyridine ring and on their nature have been established by comparison of the pK_a values of monocyclic 1,4-dihydropyridines and 4,5-dihydroindenopyridines. Additional data were obtained on the influence of the the electronic effects of sulfur-containing substitutents on the reaction center in the dihydropyridine molecules.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1228–1231, September, 1989.     

Free radicals in the electrochemical reduction of derivatives of 3,5-dinitro-1,2-dihydropyridine

The characteristics (potentials, limiting currents, reversibility) of the electrochemical reduction of 3,5-dinitro-1,2-dihydropyridines were determined by cyclic voltammetry and polarography. It was established by ESR that the free radicals formed in these processes have a radical-dianion structure in the case of both the N-unsubstituted and the N-substituted dihydropyridines. The hyperfine coupling constants of the interaction between the unpaired electron and the nuclei of the atoms at various positions of the heterocycle were determined.Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 212–218, February, 1997.     

Autoxidative transformations of 2-substituted 3-alkyl-4-hydroxy-1-oxo-1, 2-dihydroisoquinolines

A method for the preparation of 2-substituted 3-alkyl-4-hydroxy-1-oxo-1, 2-dihydroisoquinolines is described. It is shown that 2, 3-dialkyl-substituted derivatives readily undergo autoxidation and dealkylation to give N-methylphthalonimide and 3-hydroperoxy and 3-hydroxy-2, 3-dialkyl-1, 4-dioxo-1,2,3,4-tetrahydroisoquinolines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 789–792, June, 1978.     

Twist-grain boundary phase induced by Au nanoparticles in a chiral liquid crystal host

We report on the stabilisation of the liquid-crystalline, twist-grain boundary A (TGB_A) phase in mixtures of a chiral liquid crystal and surface-functionalised spherical Au nanoparticles (NPs) of 10 nm diameter. The results, obtained by calorimetric, optical, small-angle X-ray and plasmon resonance measurements, demonstrate that a TGB_A phase, which is metastable for the pure liquid crystal host, can be effectively stabilised for a 3 K range in the presence of NPs. Moreover, the role of NPs size on the TGB_A stabilisation is briefly discussed.     

Study of flame-retardant finishing of cellulose fibres: Organic–inorganic hybrid versus conventional organophosphonate

The aim of this study was to introduce a non-formaldehyde inorganic–organic hybrid sol–gel flame-retardant precursor (SiOP) containing phosphorous, nitrogen, and silicon and to compare its functional properties with those of the conventional formaldehyde-containing organic flame-retardant agent, organophosphonate (OP). SiOP was used at concentrations of 2%, 4%, and 8%, and OP was used at a concentration of 200 g/dm³. Both agents were applied to 100% cotton (CO) woven fabric by the pad-dry-cure method under the appropriate conditions. The presence of the SiOP and OP coatings on the CO fabric was confirmed by scanning electron microscopy, energy dispersive X-ray spectroscopy and Fourier-transform infrared spectroscopy. The results of the vertical tests of flammability and the thermogravimetric analyses showed that the presence of the SiOP coating changed the thermal degradation pathway of the CO fabric and resulted in an increase in the thermo-oxidative stability of the cellulose fibres. The thermo-oxidative stability was enhanced by the addition of higher amount of dry solids. At comparable dry solids contents, OP preserved significantly greater flame retardancy and thermo-oxidative stability than did SiOP. These results indicated that the SiOP precursor could not act as an effective alternative to the OP agent in the flame-retardant protection of CO fabric.     

Blue phase III widening in CE6-dispersed surface-functionalised CdSe nanoparticles

The phase transition behaviour of the chiral liquid crystal CE6 doped with spherical surface-functionalised CdSe nanoparticles has been examined by means of high-resolution adiabatic scanning calorimetry and polarising microscopy. The addition of nanoparticles results in an essentially stabilised blue phase III. The phase diagram is displayed upon heating and cooling and the enthalpy changes involved in the conversion between the blue phases are determined. The dispersion of functionalised nanoparticles is prominent for the stabilisation of blue phase III, which is potentially useful for applications, especially if applied on liquid crystals that exhibit blue phases close to room temperature.     

Novel multifunctional water- and oil-repellent,antibacterial, and flame-retardant cellulose fibres created by the sol–gel process

This research aimed to prepare cotton fibres with novel multifunctional water- and oil-repellent, antibacterial, and flame-retardant properties. A three-component equimolar sol mixture, which included 1H,1H,2H,2H-perfluorooctyltriethoxysilane, 3-(trimethoxysilyl)-propyldimethyloctadecyl ammonium chloride, and P,P-diphenyl-N-(3-(trimethoxysilyl)propyl) phosphinic amide, was applied to the cotton fabric using the sol–gel process. The presence of the coating on the cotton fibres was confirmed by Fourier transform-infrared spectroscopy and X-ray photoelectron spectroscopy. The functional properties of the coated cotton fabric were determined from liquid contact angle measurements and antibacterial activity, burning behaviour, and thermo-oxidative stability studies. The results demonstrate that a unique, compatible, and uniform organic-inorganic hybrid polymer network was formed on the fabric surface, which preserved its simultaneous hydrophobic (water contact angle of 135 ± 2°), oleophobic (n-hexadecane contact angle of 117 ± 1°), and bactericidal (bacterial reduction of 100 %) properties and incorporated the enhanced thermo-oxidative stability of the modified cellulose fibres.