CONTRIBUTION TO THE STUDY OF CIS-TRANS ISOMERS DERIVED FROM 3,3-DIPHENYL-1-HYDRINDONE. SYNTHESIS OF 3,3-DIPHENYLHYDRINDENE AND SOME OF ITS DERIVATIVES

1941 ◽  
Vol 19b (11) ◽  
pp. 275-290 ◽  
Author(s):  
Paul E. Gagnon ◽  
Ls. Phil. Charette
Keyword(s):  
Acetic Acid ◽  
Trans Isomers ◽  
Condensation Products ◽  
Chloro Derivatives ◽  
First Time ◽  
Derivatives Of

Cis-trans isomers were obtained by condensation of 3,3-diphenyl-1-hydrindone with benzaldehyde or its o- and m-methyl-, o- and p-methoxy-, o-ethoxy, o- and p-chloro-derivatives; and by conversion of the condensation products by treatment with acetic acid.3,3-Diphenyl-1-hydrindone was reduced to 3,3-diphenylhydrindene, and the condensation products of that ketone with the above mentioned aldehydes to derivatives of 3,3-diphenylhydrindene.The methods of preparation of trans- and cis-3,3-diphenyl-2-benzylidene-1-hydrindone and of 3,3-diphenylhydrindene have been improved and the following compounds are described, as far as the authors are aware, for the first time: trans- and cis-3,3-diphenyl-2-(o-methylbenzylidene)-1-hydrindone, trans- and cis-3,3-diphenyl-2-(m-methylbenzylidene)-1-hydrindone, trans- and cis-3,3-diphenyl - 2 - (o-methoxybenzylidene) - 1 - hydrindone, trans- and cis- 3,3-diphenyl-2-(p-methoxybenzylidene)-1-hydrindone, trans- and cis-3,3-diphenyl-2-(o-ethoxybenzylidene)-1-hydrindone, trans- and cis-3,3-diphenyl-2-(o-chlorobenzylidene)-1-hydrindone, trans- and cis-3,3-diphenyl-2-(p-chlorobenzylidene)-1-hydrindone, 3,3- diphenyl - 2-benzyl - hydrindene, 3,3-diphenyl - 2 - (o-methylbenzyl)-hydrindene, 3,3-diphenyl-2-(m-methylbenzyl)-hydrindene, 3,3-diphenyl-2-(o-methoxybenzyl)-hydrindene, 3,3-diphenyl-2-(p-methoxybenzyl)-hydrindene, 3,3-diphenyl-2- (o-ethoxybenzyl) - hydrindene, 3,3-diphenyl-2-(o-chlorobenzyl)-hydrindene,3,3-diphenyl-2-(p-chlorobenzyl)-hydrindene.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

Pyrimidine reactions. XXIV. The dehalogenation of 2-halogenopyrimidines by hydriodic acid

1973 ◽  
Vol 26 (2) ◽  
pp. 443 ◽  
Author(s):  
DJ Brown ◽  
P Waring
Keyword(s):  
Pure State ◽  
Hydriodic Acid ◽  
Chloro Derivatives ◽  
Amino Pyrimidine ◽  
First Time ◽  
Derivatives Of ◽  
Improved Methods ◽  
Iodo Derivative ◽  
Made In

2-Halogenopyrimidines underwent dehalogenation conveniently on treatment with hot hydriodic acid; 4,6-dimethyl-, 4,6-diphenyl-, 5- methyl-, 4-methyl-, and 4-amino-pyrimidine were so prepared from their respective 2-chloro derivatives, of which the second and third were made by improved methods; unsubstituted pyrimidine was obtained similarly from its 2-chloro, 2-bromo, or 2-iodo derivative, of which the last was made in a pure state for the first time. In contrast, 4- chloro-2,6-dimethylpyrimidine underwent hydrolysis in hot hydriodic acid and transhalogenation to give its 4-iodo analogue at lower temperatures; both 2-chloro-4-methoxy-pyrimidine and 5-chlorouracil gave uracil with hot hydriodic acid; and 4-chloro- 2,6- dimethoxypyrimidine gave 6-iodouracil under similar conditions.

Trifluoromethyl derivatives of pentagon-fused C60: 1809C60(CF3)n (n = 10, 12, 14, 16)

2021 ◽  
Author(s):  
Nadezhda B. Tamm ◽  
Vitaliy Yu. Markov ◽  
Sergey I. Troyanov
Keyword(s):  
Structural Chemistry ◽  
Chloro Derivatives ◽  
First Time ◽  
Derivatives Of

The structural chemistry of trifluoromethyl derivatives of non-IPR 1809C60 is discussed and compared with related chloro derivatives for the first time.

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.

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.

An unusual reaction of a bridged triterpenoid α-diketone with acetic anhydride

1991 ◽  
Vol 56 (12) ◽  
pp. 2917-2935 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Miloš Buděšínský ◽  
Jaroslav Podlaha ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Nmr Spectroscopy ◽  
Acetic Anhydride ◽  
Spectral Methods ◽  
X Ray Diffraction ◽  
X Ray ◽  
Mild Conditions ◽  
Condensation Products ◽  
Unsaturated Lactones ◽  
C Nmr

3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) reacts with acetic anhydride in pyridine under very mild conditions affording β-lactone IVa and γ-lactones Va and VIIa as condensation products. On reaction with pyridine, lactones Va and VIIa undergo elimination of acetic acid to give unsaturated lactones VIIIa and IXa, respectively. Similarly, the condensation of 20β,28-epoxy-21,22-dioxo-18α,19βH-ursan-3β-yl acetate (IIIb) with acetic anhydride leads to β-lactone IVb and γ-lactone Vb; the latter on heating with pyridine affords unsaturated lactone VIIIb and 21-methylene-22-ketone Xb. The structure of the obtained compounds was derived using spectral methods, particularly 1H and 13C NMR spectroscopy; structure of lactone IVa was confirmed by X-ray diffraction.

ChemInform Abstract: DIHALO DERIVATIVES OF NAPHTHOSTYRIL-N-ACETIC ACID

1978 ◽  
Vol 9 (34) ◽  
Author(s):  
A. P. KARISHIN ◽  
A. A. PECHKA ◽  
N. F. GRINEVA
Keyword(s):  
Acetic Acid ◽  
Derivatives Of
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