2',3'-O-Carbonyl derivatives of 6-azauridine in the synthesis of its 5-substituted and 5'-deoxy derivatives

1987 ◽  
Vol 52 (8) ◽  
pp. 2070-2082
Author(s):  
Pavel Drašar ◽  
Jiří Beránek
Keyword(s):  
Thionyl Chloride ◽  
Alkaline Hydrolysis ◽  
Triphenyl Phosphine ◽  
Carbonyl Derivatives ◽  
Tributyltin Hydride ◽  
Chloro Derivative ◽  
Ammonium Halides ◽  
Chloro Derivatives ◽  
Derivatives Of ◽  
Dichloro Derivative

Preparation of 2',3'-O-carbonyl derivatives of 5'-deoxy-6-azauridine and 6-azauridine using 1,1'-carbonyldiimidazole has been elaborated. 5'-Chloro and 5'-bromo derivatives were prepared by treatment of the 5'-O-mesyl derivative with quaternary ammonium halides, 5'-chloro derivatives also by direct halogenation with thionyl chloride in hexamethylphosphortriamide or with tetrachloromethane, triphenyl phosphine, and dimethylformamide. Derivatives of 5'-bromo-6-azauridine were reduced with tributyltin hydride to 5'-deoxy-6-azauridine compounds. 6-Azauridine 2',3'-carbonate (IVa) and its 5'-derivatives IVc and IVe on treatment with imidazole in dimethylformamide afforded 2,2'-anhydronucleosides IIIa-IIIc. The 2,2'-anhydro-5'-deoxy compound IIIc underwent alkaline hydrolysis to 5'-deoxy-1-β-D-arabino-pentofuranosyl-6-azauracil (VIa). Treatment of 2,2'-anhydro-5'-deoxy-5'-chloro derivative IIIb with hydrogen chloride led to 2',5'-dichloro derivative If.

Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

1984 ◽  
Vol 49 (1) ◽  
pp. 110-121 ◽  
Author(s):  
Jiří Křepelka ◽  
Drahuše Vlčková ◽  
Milan Mělka
Keyword(s):  
Thionyl Chloride ◽  
Oxirane Ring ◽  
Secondary Amines ◽  
Two Phase ◽  
Lytic Effect ◽  
Primary And Secondary Amines ◽  
Phase Medium ◽  
Chloro Derivatives ◽  
Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

Neuartige Allylboran- und Allyldiboran(4)-Derivate / Novel Allylboran- and Allyldiboran(4) Derivatives

1990 ◽  
Vol 45 (7) ◽  
pp. 985-988 ◽  
Author(s):  
Gabriele Knörzer ◽  
Hermann Seyffer ◽  
Hans Pritzkow ◽  
Walter Siebert
Keyword(s):  
Structure Analysis ◽  
X Ray ◽  
Chloro Derivative ◽  
Chloro Derivatives ◽  
Derivatives Of

Allyldiboran(4) derivatives la—c are obtained from allylmagnesium chloride and chloro derivatives of diboran(4). la—c are air-sensitive liquids; heating of le did not yield a 2,3-dihydro-l,2-diborole derivative (B). Reaction between 1,1-bis(dichloroboryl)-3,3-dimethyl-butane (5) and H2C=C(CH2SnMe3)2 (4) leads to the heat-sensitive chloro derivative 2a, in which the chlorine is substituted by Me3SiNMe2 to give stable 1,3-bis-dimethylamino-5-methylene-2-neopentyl- 1,3-diborinane (2 b). 1,2-Bis(dichloroboryl)benzene and 4 yield the chloro derivative 3a, and its substitution with HN(i-Pr)2 leads to 1,4-bis(diisopropylamino)-2,3-benzo-6-methylene-1,4,5,7-tetrahydro-1,4-diborepine (3 b). The X-ray structure analysis reveals a folded tetrahydro-1,4-diborepine ring.

Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines

2006 ◽  
Vol 60 (3) ◽  
Author(s):  
M. Búdová ◽  
K. Fojtíková ◽  
J. Miklovič ◽  
V. Mrázová ◽  
B. Horváth ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrazine Hydrate ◽  
Chlorine Atom ◽  
Phosphorus Oxychloride ◽  
Sodium Ethoxide ◽  
Secondary Amines ◽  
Chloro Derivative ◽  
Chloro Derivatives ◽  
Derivatives Of

AbstractSubstituted furopropenoic acids were prepared from appropriate aldehyde under the Doebner’s conditions. Obtained acids were converted to the corresponding azides, which were cyclized by heating in Dowtherm to furopyridones. These compounds were aromatized with phosphorus oxychloride to chloro derivatives of furo[3,2-c]pyridine (Va, Vb). Chloro derivative Vb was reduced with hydrazine hydrate to 2-(4-aminophenyl)furo[3,2-c]pyridine in ethanol and Pd/C as a catalyst. Chloro derivative Va was converted to 4-amino-2-(3-pyridyl)furo[3,2-c]pyridine under the same conditions. The chlorine atom in other chloro derivatives (VIIa, VIIb) was replaced by nucleophilic substitution with alkoxides (sodium ethoxide, propoxide, and isopropoxide) and the corresponding alkoxy derivatives were formed. By reaction of VII with cyclic secondary amines (morpholine, piperidine, and pyrrolidine) 4-substituted furopyridines were prepared.

Reaction of nucleosides with thionyl chloride; Preparation of the deoxy derivatives of cytidine and adenosine

1980 ◽  
Vol 45 (2) ◽  
pp. 599-605 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Josef Brokeš ◽  
Jiří Beránek
Keyword(s):  
Cell Growth ◽  
Thionyl Chloride ◽  
Inhibitory Effect ◽  
L1210 Cell ◽  
Quantitative Yield ◽  
Dimethyl Formamide ◽  
Tributyltin Hydride ◽  
Derivatives Of

On reaction of thionyl chloride with cytidine and adenosine in refluxing acetonitrile, the 5' -chloro-2',3' -sulphinyl derivatives I and VII are formed in a quantitative yield. On heating in dimethyl-formamide, compound I affords 5' -chloro-5' -deoxycyclocytidine (II) which is hydrolyzed in alkali to the arabinosyl derivative III; reduction of III with tributyltin hydride gives the 5' -deoxyarabinosyl derivative IV. The sulphinyl derivative I is hydrolyzed to 5' -chloro-5' -deoxycytidine (V) which is reduced to 5' -deoxycytidine (VI). Analogously, the sulphinyl derivative VII affords 5' -chloro-5' -deoxyadenosine (VIII) and the reduction of VIII gives 5' -deoxyadenosine (IX). Of these compounds, the 5' -chloro-5' -deoxyarabinosyl derivative as the only one shows an inhibitory effect towards the L1210 cell growth.

scholarly journals Synthesis and Spectroscopic Studies of Some New Molybdenum, Tungsten, and Ruthenium Carbonyl Derivatives of 2-Hydroxymethylpyridine

2010 ◽  
Vol 2010 ◽  
pp. 1-6 ◽  
Author(s):  
M. A. Taher ◽  
S. E. Jarelnabbi ◽  
B. E. Bayoumy ◽  
S. M. El-Medani ◽  
R. M. Ramadan
Keyword(s):  
Mass Spectrometry ◽  
Thermal Properties ◽  
Spectroscopic Studies ◽  
Triphenyl Phosphine ◽  
Tricarbonyl Complex ◽  
Thermal Reactions ◽  
Carbonyl Derivatives ◽  
Ir And Nmr Spectroscopy ◽  
Ruthenium Carbonyl ◽  
Derivatives Of

Thermal reactions of 2-hydroxymethylpyridine (HMP) with [M(CO)6] in air resulted in formation of the oxo-complexes [M2O6(HMP)2], where M = Mo, 1, or W, 2. The tricarbonyl complex [Ru(CO)3(HMP)], 3, was obtained from the reaction of [Ru3(CO)12] with HMP. In presence of triphenyl phosphine (PPh3), the reaction of HMP with Ru3(CO)12 gave [Ru(CO)2(HMP)(PPh3)], 4. All the complexes were characterized by elemental analysis, mass spectrometry, IR, and NMR spectroscopy. The thermal properties of the complexes were also investigated by thermogravimetry technique.

Chemical behaviour of dicyanocob(III)yrinic acid heptamethyl ester and cob(I)yrinic acid heptamethyl ester in some preparative experiments

1976 ◽  
Vol 273 (924) ◽  
pp. 327-333 ◽  
Keyword(s):  
Absorption Spectra ◽  
Electronic Absorption ◽  
Electronic Absorption Spectra ◽  
Chloro Derivative ◽  
Chemical Behaviour ◽  
Chloro Derivatives ◽  
Derivatives Of

Preparations of CIO acetate, trifluoroacetate, and chloro derivatives of dicyano-cobyrinic acid heptamethyl ester (‘cobester’) are described. The nature and properties of intermediates in the synthesis of the 10-chloro derivative are discussed, and the electronic absorption spectra of the products are presented.

1-[3-(2-Alkoxyphenoxy)-3-phenylpropyl]piperazines and some related compounds

1981 ◽  
Vol 46 (5) ◽  
pp. 1280-1287 ◽  
Author(s):  
Vladimír Valenta ◽  
Marie Bartošová ◽  
Miroslav Protiva
Keyword(s):  
Thionyl Chloride ◽  
Alkaline Hydrolysis ◽  
Mannich Bases ◽  
Ethyl Chloroformate ◽  
Substitution Reactions ◽  
Sodium Salts ◽  
Specific Effects ◽  
Chloro Derivatives ◽  
High Doses ◽  
Related Compounds

Amino alcohols VIIIa-c, prepared by reduction of the Mannich bases VIa-c, were transformed by treatment with thionyl chloride to the chloro derivatives IXa-c which were subjected to substitution reactions with the sodium salts of guaiacol, 2-ethoxyphenol and 2-benzyloxyphenol giving the title compounds IIIb,c, IVb,c and Va-c. N,N-Dimethyl-3-(2-benzyloxyphenoxy)-3-phenylpropylamine (Va) was partially demethylated by treatment with ethyl chloroformate and by the following alkaline hydrolysis to the secondary amine XI. Amines III-V and XI in high doses exhibit central excitation but do not show antireserpine activity; they have several structurally less specific effects (hypotensive, local anaesthetic, spasmolytic).

Toxicity of Para-Chloro Substituted Benzene Derivatives in the Microtox™ Test

1985 ◽  
Vol 20 (2) ◽  
pp. 36-43 ◽  
Author(s):  
Klaus L.E. Kaiser ◽  
Juan M. Ribo ◽  
Brian M. Zaruk
Keyword(s):  
General Formula ◽  
Functional Group ◽  
Structural Parameters ◽  
Systematic Investigation ◽  
Photobacterium Phosphoreum ◽  
Benzene Derivatives ◽  
Quantitative Structure ◽  
Chlorinated Benzenes ◽  
Chloro Derivatives ◽  
Derivatives Of

Abstract This paper gives the results of part of a systematic investigation into contaminant toxicity to Photobacterium phosphoreum in the Microtox™ test. Reported are the toxicity values for 39 para-chloro substituted benzene derivatives of the general formula l-Cl-C6h4-4-X=CH2CH(NH2)COOH, F, SO2NH2, OCH2COOH, CH2COOH, CONHNH2, NHCOCH3, CONH2, CH=CHCOOH, SeOOH, CH2NH2, CH2CH2NH2, NO2, H, CF3, CHO, CH2OH, OH, CH3, CCl3, COCH3, COOH, NH2, SO2C6H5, Cl, CH2COCH3, COCl, CN, OCH3, NCO, NHCH3, I, COC6H5, CH2Cl, SH, CH2SH, NCS, CH2CN and SO2C6H4Cl. Except for the last compound, whose solubility is below the required concentration, the toxicities increase in the presented order with a total range of more than three orders of magnitude. The data are discussed in terms of quantitative structure-toxicity correlations with compound-specific structural parameters. In combination with a previously developed submodel on chlorinated benzenes, phenols, nitrobenzenes and anilines, the observed relationships allow the prediction of the toxicity of some 780 possible chloro derivatives of the general formula C6H5-nClnX, where n=<5 and X is a functional group as listed above.

Some 6-substituted derivatives of D-8-cyanomethylergoline-I and D-8-methylergoline-I

1979 ◽  
Vol 44 (3) ◽  
pp. 946-951 ◽  
Author(s):  
Antonín Černý ◽  
Jiří Křepelka ◽  
Miroslav Semonský
Keyword(s):  
Inhibiting Activity ◽  
Chloro Derivatives ◽  
Derivatives Of

Compounds III-XX exhibiting antilactation and antinidation effects in tests on rats were prepared on N(6)-alkylation of D-8-cyanomethylergoline-I (I) or D-8-methylergoline-I (II) with corresponding bromo (chloro) derivatives in dimethylformamide. The most distinct prolactin-inhibiting activity was found in compound III.

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