Nitroimidazoles X . Syntheses of substituted 2-(1-methyl-5-nitro-2-imidazolyl)quinolines

Reduction of substituted-2-nitrobenzaldehyde (1) afforded substituted-2-aminobenzaldehyde (2) . Reaction of compound 2 with 2-acetyl-1-methyl-5-nitroimidazole (3) under basic conditions afforded substituted 2-(1-methyl-5-nitro-2-imidazolyl)quinolines 4 . Reaction of compound 4 (R = X) with hydrogen peroxide in acetic acid afforded compound 5 which was transformed to compound 6 with phosphorus oxychloride.     

Chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)-thio]purine (azathioprine)

The chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine (azathiopurine) —hydrogenation, acetylation, alkylation by lower alkyl halides at positions 7 and 9 of the purine ring, hydrolytic cleavage at the C₍₆₎–S and S–C₍₅₎ bonds— were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 372–379, March, 2000.     

Synthesis of 3-fluoro-2-(trinitromethyl)-1-propanol

Conclusions 3-Fluoro-2-(trinltromethyl)-1-propanol nitrate, the acid hydrolysis of which resulted in 3-fluoro-2-(trinitromethyl)-1-propanol, was obtained by the direct fluorination of 2,4-bis(trinitromethyl)-4-mercuri-1,7-heptanediol.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1650–1651, July, 1972.     

2-甲基-N-[4-硝基-3-三氟(甲基)苯基]丙酰胺的改进合成

以3－三氟里基苯为原料,在吸酸剂碳酸氢钠作用下与2－甲基丙酰氯反应得到2－甲基－N－[4－硝基－3－三氟（甲基）苯基]丙酰胺,再进行混酸硝化得到目标化合物。     

The reaction of 3-(1-imidazolyl)-2-alken-1-ones with nucleophiles

Generally 3-hetero-substituted 2-alken-1-ones were prepared from 1,3-alkanediones, 3-chloro-2-alken-1-ones, or conjugated ynones. The preparation of 3-hetero-substituted 2-alken-1-ones was subjected to some limitations by these methods. By the reaction of 3-(1-imidazolyl)-2-alken-1-ones (I) and 3-(3-oxo-1-alkenyl)-1-methylimidazolium iodides (II) with nucleophiles, 3-hetero-substituted 2-alken-1-ones could be obtained regioselectively in good yield under mild conditions. These results suggested that compounds I and II were concluded to be useful intermediates for the organic synthesis.     

Butyl vinyl ether-1-amino-3-[2-(vinyloxy)ethoxy]-2-propanol cooligomer as a stabilizer of mazut-coal blended fuel

Butyl vinyl ether-1-amino-3-[2-(vinyloxy)ethoxy]-2-propanol cooligomer was prepared and studied as a stabilizer of mazut-coal blended fuel.     

Synthesis and structural characterization of 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride

In the course of studies on hybrid antibacterials incorporating 2-aryl-5-nitro-1H-indole moieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurally characterized. This pyridinium chloride salt crystallized in the monoclinic space group P2(1)/c with the following unit cell dimensions: a 10.274(3) ?, b 13.101(4) ?, c 13.439(4) ?, b 107.702(7)°, V 1723.2(9) ?3, Z (f.u.) = 4; R1 = 0.048, and wR2 = 0.13. Of interest in the single crystal X-ray structure is the (intramolecular) disposition of the pyridinium plane over the indole heterocyclic residue [interplanar dihedral angle 17.91(4)°].     

COPPER(II) COMPLEXES OF 1-[O-ALLYLPHENOXY]-3-[ISOPROPYLAMINO]-2-PROPANOL (ALPRENOLOL)

Abstract

Complexation of Cu(II) with the antihypertension drug Alprenolol (HAlp) under different conditions (metal/ligand ratios and solvents) results in the formation of two complexes - a binuclear green one, Cu₂Alp₂Cl₂ (1), and a mononuclear violet species CuAlp₂·2H₂O (2). Single crystals of (1) were isolated and its structure determined by X-ray diffraction. In the complex Alprenolol molecules are bidentately coordinated and each Cu atom is bound with NH, and bridged by the deprotonated OH group of the ligand to the second Cu centre. The chloride ions are coordinated to copper as terminal ligands. The mononuclear complex (2) was characterized using electronic and IR spectra, EPR, magnetochemical, calorimetric, thermogravimetric methods and elemental analysis. Copper is coordinated through O^? and N of OH and NH groups of the ligands in a distorted tetrahedral structure. The structure includes also two solvent molecules per CuAlp₂ unit.     

Preparation of 2(3)-O-[2-(hydroxyamino)-2-oxoethyl]- and 2(3)-O-[3-(hydroxyamino)-3-oxopropyl]dextran

Hydroxame derivatives of carboxymethyl- and carboxyethyldextrans have been prepared and characterized by elemental analysis as well as by IR and UV spectroscopy. The effect of reaction conditions on the products yield has been studied.     

Synthesis of 1-halophenyl 4-(2-imidazolyl)-1-butanones and 5-(2-imidazolyl)-1-pentanones and their ketalization with glycerol

An alternate synthesis of 1-(2,4-dichlorophenyl)-4-(2-imidazolyl)-1-butanones 5d is presented after 1-[(dimethylamino)methyl- and 1-methyl]-2-lithioimidazole failed to be substituted satisfactorily by 2-(2,4-dichlorophenyl)-2-(3-iodopropyl)-1,3-dioxolane ( 3b ). The Pinner addition of ethanol to 2-(2,4-dichlorophenyl)-2-(3-cyanopropyl)-1,3-dioxolane yielded the corresponding imidate which was reacted with 1-amino-2,2-dimethoxyethane to form an amidine. Hot dilute hydrochloric acid converted this ami-dine to the 2-imidazolyl ketone 5b . Syntheses of homologous 1-(4-chloro- and 2,4-dichlorophenyl)-4-(2-imidazolyl)-1-pentanones 20 are described. Ketalizations of 5 and 20 with glycerol formed imidazolyl 1,3-dioxolanyl alcohols. Selective N- and O-alkylations of some of these imidazolyl alcohols are described.