Potential hypnotics and anxiolytics: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl)piperazino]-methyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and related compounds

1983 ◽  
Vol 48 (12) ◽  
pp. 3433-3443 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Jan Metyš ◽  
Zdeněk Šedivý ◽  
Miroslav Protiva
Keyword(s):  
Hydrazine Hydrate ◽  
Title Compound ◽  
Acid Hydrazide ◽  
Ethyl Esters ◽  
Ethyl Chloroacetate ◽  
Related Compounds ◽  
Central Depressant

Ethyl esters of 4-substituted piperazinoacetic acids IIIa-f were prepared by alkylation of 1-(ethoxycarbonylmethyl)piperazine with 2-methoxyethyl bromide, 2-ethoxyethyl bromide, 2-methylthioethyl chloride, 2-phenoxyethyl bromide and 2-phenylthioethyl bromide or by reactions of 1-(3-methoxypropyl)piperazine and 1-(2-methylthioethyl)piperazine with ethyl chloroacetate. Reactions of the esters with hydrazine hydrate gave the hydrazides IVa-f. Their treatment with 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-thione resulted in the title compound Ia and analogues Ib-f. 1-(4-Methylpiperazinomethyl) derivatives Ig and IIg were similarly prepared from 4-methylpiperazinoacetic acid hydrazide (IVg). Compound Ig showed significant central depressant and anticonvulsant (electroshock) activity in mice. The enlargement of the substituent in position 4 of the piperazine residue results in an important decrease of these activities.

Neuroleptic agents derived from perathiepin: 6,7-Dichloro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin and related compounds

1981 ◽  
Vol 46 (7) ◽  
pp. 1607-1613 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Benzoic Acid ◽  
Title Compound ◽  
Titanium Tetrachloride ◽  
Substitution Reactions ◽  
Related Compounds ◽  
Hydroxyethyl Piperazine ◽  
Central Depressant ◽  
Dichloro Derivative ◽  
Iodobenzoic Acid

The reaction of 2,3-dichlorothiophenol with 2-iodobenzoic acid gave 2-(2,3-dichlorophenylthio)benzoic acid (V) which was transformed in four steps to the homological acid IX. Cyclization resulted in 6,7-dichlorodibenzo[b,f]thiepin-10(11H)-one (X) which was converted via the alcohol XI to the trichloro compound XII. Substitution reactions of XII with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine afforded the title compound I and its hydroxyethyl analogue II. Reaction of the ketone X with 1-methylpiperazine and titanium tetrachloride gave the enamine III. Compounds I-III exhibit mild central depressant and relatively strong cataleptic activity.

Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds

1983 ◽  
Vol 48 (2) ◽  
pp. 623-641 ◽  
Author(s):  
Zdeněk Polívka ◽  
Miroslav Rajšner ◽  
Jan Metyš ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
...  
Keyword(s):  
Clinical Trials ◽  
Sulfuric Acid ◽  
Title Compound ◽  
Amino Alcohol ◽  
Hydrogen Sulfate ◽  
Geometric Isomers ◽  
Pure Alcohol ◽  
Acid Catalyzed ◽  
Anticataleptic Activity ◽  
Related Compounds

In the reaction of thieno[2,3c]-2-benzothiepin-4(9H)-one (VI) with 1-methyl-4-piperidylmagnesium chloride 7-(1-methyl-4-piperidyl)thieno[2,3-c]-2-benzothiepin-4(9H)-one (VIII) is formed in addition to the expected amino alcohol VII. The title compound I was obtained by the acid catalyzed dehydration of the pure alcohol VII. Compound I (pipethiadene) has outstanding antihistamine, antiserotonin, antireserpine and anticataleptic activity and was recommended to clinical trials as a potential antimigraine agent. For pharmacokinetic and metabolic studies there were prepared the NC2H3 analogue of pipethiadene IV and further, as potential metabolites, the demethyl analogue III, S-oxide X, demethyl S-oxide XI, N-oxide XIII and N,S-dioxide XIV. The Witting reaction of the ketone VI with 3-dimethylaminopropylidenetriphenylphosphorane resulted in a mixture of geometric isomers of 4-(3-dimethylamino-propylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin with the strongly predominating Z-isomer XVI which was isolated from the mixture by crystallization of the hydrogen maleate. The mixture with the predominating Z-isomer XVI was converted by the treatment with 80% sulfuric acid and dilution with water to a mixture with the predominating E-isomer XV (dithiadene) which was isolated by crystallization of the hydrogen sulfate. Some further new thieno[2,3-c]-2-benzothiepin derivatives were synthesized as potential intermediates.

Experimental evidence for the amino-group non-planarity in nitroanilines: neutron diffraction study of 2-methyl-5-nitroaniline at 100 K

1999 ◽  
Vol 55 (2) ◽  
pp. 209-215 ◽  
Author(s):  
Javier Ellena ◽  
Andrés E. Goeta ◽  
Judith A. K. Howard ◽  
Chick C. Wilson ◽  
Juan C. Autino ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Neutron Diffraction ◽  
Experimental Evidence ◽  
Diffraction Study ◽  
Title Compound ◽  
Neutron Diffraction Study ◽  
Amino Group ◽  
X Ray ◽  
Related Compounds ◽  
Centrosymmetric Dimers

An appreciable degree of pyramidalization of the amine N atom is observed in the title compound. The existence of polar chains, induced by N—H...O synthons, is confirmed. C—H...O interactions, not noted in a previous X-ray study, were found to stabilize further the known head-to-tail assembling of the chains. The structure can be described as non-polar (101) layers, embodying chains interlinked by centrosymmetric dimers, connected by C(aryl)—H...π interactions. The latter are not present in m-nitroaniline, 2-methyl-4-nitroaniline and other related compounds with chains built from similar N—H...O synthons and assembled head-to-head. This finding implies that an obvious relationship between molecular recognition patterns and crystal structures should not be assumed.

scholarly journals 6-[1-Acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-3-yl]-2(3H)-benzoxazolone

Molbank ◽  
10.3390/m1021 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1021
Author(s):  
Yordanka Ivanova ◽  
Antonya Todorova ◽  
Christo Chanev ◽  
Ognyan Petrov
Keyword(s):  
Acetic Acid ◽  
Hydrazine Hydrate ◽  
1H Nmr ◽  
Elemental Analysis ◽  
13C Nmr ◽  
Title Compound ◽  
Target Compound

The title compound, 6-[1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2(3H)-benzoxazolone, was synthesized by condensation of 6-[3-(4-methoxyphenyl)-2-propenoyl]-2(3H)-benzoxazolone (1) and hydrazine hydrate in acetic acid in 84% yield. The structure of the target compound was confirmed using 1H-NMR, 13C-NMR, IR, MS, and elemental analysis.

(1E,2E)-1,2-Bis[(E)-3-phenylallylidene]hydrazine

2007 ◽  
Vol 63 (11) ◽  
pp. o4443-o4443
Author(s):  
Xiao-Hua Chen
Keyword(s):  
Hydrazine Hydrate ◽  
Title Compound ◽  
Inversion Center ◽  
Planar Molecule

The title compound [alternatively called (E)-3-phenylprop-2-enal azine], C18H16N2, was synthesized by the reaction of hydrocinnamaldehyde with hydrazine hydrate. The nearly planar molecule is centrosymmetric, with the mid-point of the N—N bond lying at an inversion center.

Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds

1990 ◽  
Vol 68 (11) ◽  
pp. 1917-1922 ◽  
Author(s):  
Réjean Ruel ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Michael Addition ◽  
Title Compound ◽  
Steroid Synthesis ◽  
Related Compounds ◽  
Acetylenic Ketone

The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

scholarly journals Crystal structure ofO-ethylN-(ethoxycarbonyl)thiocarbamate

2015 ◽  
Vol 71 (10) ◽  
pp. o782-o783 ◽  
Author(s):  
Matthew J. Henley ◽  
Alex M. Schrader ◽  
Victor G. Young ◽  
George Barany
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Least Squares ◽  
Title Compound ◽  
Compound C ◽  
The One ◽  
Related Compounds ◽  
Centrosymmetric Dimers

The title compound, C6H11NO3S, provides entries to novel carbamoyl disulfanes and related compounds of interest to our laboratory. The atoms of the central O(C=S)N(C=O)O fragment have an r.m.s. deviation of 0.1077 Å from the respective least-squares plane. While several conformational orientations are conceivable, the crystal structure shows only the one in which the carbonyl and the thiocarbonyl moieties areantito each other across the central conjugated C—N—C moiety. Pairs of 2.54 Å N—H...S=C hydrogen bonds between adjacent molecules form centrosymmetric dimers in the crystal.

scholarly journals Di-tert-butyl 1-[2-hydroxy-3-(methylsulfanyl)propyl]hydrazine-1,2-dicarboxylate

2014 ◽  
Vol 70 (8) ◽  
pp. o843-o843
Author(s):  
Xiao-Guang Bai ◽  
Xiao-Yu Yang ◽  
Ju-Xian Wang
Keyword(s):  
Hydrogen Bonds ◽  
Hydrazine Hydrate ◽  
Title Compound ◽  
Axis Direction ◽  
Tert Butyl ◽  
Compound C ◽  
Supramolecular Chains

The title compound, C14H28N2O5S, was synthesized by the reaction of 2-[(methylsulfanyl)methyl]oxirane with di-tert-butyl oxalate in hydrazine hydrate. In the crystal, molecules are linked by N—H...O and O—H...O hydrogen bonds into supramolecular chains propagating along theb-axis direction.

Conformational analysis of the products of 1,4 addition of Tri(phenylthio)methyllithium to α,β-unsaturated ketones. The X-ray structuredetermination of 4-Phenyl-5,5,5-tri(phenylthio)pentan-2-one

1981 ◽  
Vol 34 (12) ◽  
pp. 2671
Author(s):  
AB Manas ◽  
RAJ Smith ◽  
J Simpson
Keyword(s):  
Conformational Analysis ◽  
Dihedral Angle ◽  
Spin System ◽  
Title Compound ◽  
Second Order ◽  
Coupling Constants ◽  
X Ray ◽  
Unsaturated Ketones ◽  
Iterative Analysis ◽  
Related Compounds

Iterative analysis of the second-order ABX spin system in the 1H n.m.r. of the title compound gave coupling constants which are consistent with a conformation involving a H-C-C-H dihedral angle of about 90�. The structure was confirmed by X-ray analysis. The 1H n.m.r. of the related compounds 2,2-dimethyl-5-pheny1-6,6,6-tri(phenylthio)hexan-3-one and 1,3-diphenyl-4,4,4-tri(pheny1-thio)butan-1-one were also analysed and found to have similar conformational characteristics.

scholarly journals An Efficient and Mild Method for the Synthesis and Hydrazinolysis ofN-Glyoxylamino Acid Esters

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Ayman El-Faham ◽  
Zainab Al Marhoon ◽  
Ahmed Abdel-Megeed ◽  
Mohamed Siddiqui
Keyword(s):  
Hydrazine Hydrate ◽  
Good Yield ◽  
Acid Ester ◽  
Ring Opening ◽  
Acid Hydrazide ◽  
Type Reaction ◽  
H Nmr ◽  
Elemental Microanalysis ◽  
Acid Esters ◽  
C Nmr

N-Glyoxylamino acid ester derivatives were synthesized via the ring opening ofN-acetylisatin using moderate conditions. During the hydrazinolysis ofN-glyoxylamino acid ester derivatives with hydrazine hydrate (80%) in methanol, unexpected reduction of theα-keto group occurred to affordN-acylamino acid hydrazide derivatives in good yield (80–90%) (Wolff-Kishner type reaction). All the synthesized compounds were characterized by1H NMR,13C NMR, and elemental microanalysis.

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