M. N. Zemtsova

Synthesis and antiviral activity of several quinoline derivatives

The antiviral activity of 2-substituted and 2,6-disubstituted quinoline-4-carboxylic acids and their derivatives has been studied against orthopoxviruses on Vero and MK-2 cell cultures. High activity has been found for 2-(1,1′-biphenyl-4-yl)quinoline-4-carboxylic acid.

Synthesis of substituted 1,2,3,4-tetrahydroquinoline-4-carboxylic acids

Reduction of some substituted quinoline-4-carboxylic acids was studied. The reduction of 2-alkylquinoline-4-carboxylic acids with Raney nickel in aqueous alkali was stereoselective, and the resulting 2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic acids were individual cis isomers.

Adamantanol nitrates in nucleophilic substitution reactions

ConclusionsFunctional derivatives of alkyladamantanes may be obtained in good yields from the corresponding alkyladamantanol nitrates.

Synthesis of alkyladamantol nitrates

Conclusions1.Alkyladamantanol nitrates are formed by the treatment of the corresponding alkyl-adamantanes with fuming nitric acid.2.The hydrolysis of alkyladamantanol nitrates by dilute nitric acid gives the corresponding alkyladamantanols.

Bromination of 2-phenyl-1,2,3,4-tetrahydroquinolines

Bromination of 2-phenyltetrahydroquinolines derivatives was investigated. During the bromination of 2-phenyl-1,2,3,4-tetrahydroquinoline with bromine in chloroform or bromosuccinimide along with the formation of di- and tribrom derivatives the oxidation reaction occurs with the generation of quinoline structure. The interaction of 2-phenyl-1,2,3,4-tetrahydroquinoline with bromine in acetic acid leads to the formation of 6,8-dibromoderivative preserving the 1,2,3,4-tetrahydroquinoline ring. At the same time N-substituted 2-phenyl-1,2,3,4-tetrahydroquinoline is selectively brominated in various conditions with the formation of 6-monobromoderivative. By the method of X-ray diffraction analysis the molecular structure of 3,6,8-tribromo-2-phenylquinoline single crystals was determined.

Synthesis and antituberculous activity of quinoline isosteres of isoniazid

We present an evaluation of the antimycobacterial activity of a series of 2-aryl(heteryl)-4-quinolinecarboxylic acids. Compounds with potential value against Mycobacterium tuberculosis H37Rv were found.

Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.

In the title molecule, C14H15NO3, the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C—H⋯π interactions link the molecules into centrosymmetric dimers, and weak intermolecular C—H⋯O hydrogen bonds link these dimers into columns propagated along [100].

Synthesis of Z-2-methyl-6-R-1,2,3,4-tetrahydro-4-quinolinecarboxylic acids

The known methods of reduction of quinolinecarboxylic acids not always give high yields of 1,2,3,4-tetrahydroquinolinecarboxylic acids and often involve a formation of product mixtures [1, 2]. We discovered an effi cient procedure for the synthesis of 2-methyland 2,6-dimethyl-1,2,3,4-tetrahydro-4quinolinecarboxylic acids (I and II). 2-Methyl-1,2,3,4-tetrahydroquinoline-4-carboxylic acid (I). To a solution of 2 g (0.01 mol) of 2-methylquinoline-4-carboxylic acid in 10 ml of 10% sodium hydroxide was added by small portions at stirring within 1 h 1.6 g of Raney alloy, and the mixture was stirred for 1 h more at room temperature. The precipitate was fi ltered off, washed with hot water, formic acid was added to the fi ltrate to pH 3, and the reaction product was extracted into chloroform and dried over anhydrous sodium sulfate. Chloroform was evaporated to dryness, and the residue was recrystallized from 50% ethanol. Yield 1.6 g (80%), colorless crystals, mp 131–134°C. IR spectrum, ν, cm–1: 1701 (CO), 2966 (CH3), 3278 (NH). 1H NMR spectrum, δ, ppm: 1.29 d (3H, CH3, J 6.11 Hz), 2.01 d.d (1H, H3a, J 12.21, 10.98 Hz), 2.26 d.d.d (1H, H3e, J 10.98, 6.11, 2.44 Hz), 3.45 d.d.d (1H, H2a, J 10.98, 6.11, 2.44 Hz), 4.01 d.d (1H, H4a, J 12.21, 6.11 Hz), 6.56 d (1H, H8, J 7.33 Hz), 6.71 t (1H, H6, J 7.33 Hz), 7.07 t (1H, H7, J 7.33 Hz), 7.14 d (1H, H5, J 3.33 Hz). Mass spectrum, m/z (Irel, %): 205 (44) [M]+, 190 (28), 146 (91), 130 (100), 118 (9.5), 103 (4), 77 (19), 65 (8). Found, %: C 69.00; H 6.87; N 7.40. C11H13NO2. Calculated, %: C 69.11; H 6.80; N 7.33. 2,6-Dimethyl-1,2,3,4-tetrahydroquinoline-4carboxylic acid (II) was prepared similarly. Yield 85%, mp 136–140°C (50% ethanol). IR spectrum, ν, cm–1: 1716 (CO), 2950, 2854 (CH3), 3382 (NH). 1H NMR spectrum, δ, ppm: 1.29 d (3H, CH3, J 6.3 Hz), 1.8 d.d (1H, H3a, J 12.3, 11.1 Hz), 2.11 s (3H, CH3), 2.2 d.d.d (1H, H3e, J 11.3, 7.11, 2.6 Hz), 3.35 d.d.d (1H, H2a, J 11.11, 6.58, 2.4 Hz), 3.85 d.d (1H, H4a, J 12.5, 6.6 Hz), 6.4 d (1H, H8, J 8.1 Hz), 6.8 d (1H, H7, J 8.33 Hz), 7.4 s (1H, H5). Mass spectrum, m/z (Irel, %): 219 (45) N

Synthesis and structure of methyl 8-allyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-4-carboxylate

The compound C15H18NO2Br was synthesized and characterized by X-ray diffraction. The crystals belong to the monoclinic system, sp. gr. P21/n, a = 8.913(2) Å, b = 23.637(6) Å, c = 13.892(3) Å, β = 90.31(2)°, Z = 8, V = 2926.8(12) Å3, ρcalc = 1.472 g/cm3. The bond lengths and bond angles in two molecules are equal within an experimental error and are typical of this class of compounds. The conformational differences of the saturated heterocyclic and methoxycarbonyl fragments of the molecules result in the presence of two crystallographically independent molecules in the crystal structure.

2,6-Dimethyl-4-(1,3,4-oxadiazol-2-yl)quinoline.

The title compound, C13H11N3O, a potential chemotherapeutic agent, contains a essential planar [maximum deviation = 0.0144 (14) Å] quinoline moiety. The quinoline ring system and the five-membered heterocycle form a dihedral angle of 7.81 (6)°. In the crystal, intermolecular non-classical C—H⋯N hydrogen bonding is present.