Potent neuroleptic agents: Some new amino alcohols of the 10-piperazinodibenzo[b,f]thiepin series and their derivatives

1976 ◽  
Vol 41 (2) ◽  
pp. 443-458 ◽  
Author(s):  
J. O. Jílek ◽  
I. Červená ◽  
Z. Kopicová ◽  
K. Šindelář ◽  
E. Svátek ◽  
...  
Keyword(s):  
Amino Alcohols

Synthesis of the semi-rigid analogues of prothiadene and dithiadene as potential antidepressant and antihistamine agents: 11-[2-(Dimethylaminomethyl)cyclohexylidene]-6,11-dihydrodibenzo[b,e]thiepins and 4-[2-(dimethylaminomethyl)cyclohexylidene]-4,9-dihydrothieno-[2,3-c]-2-benzothiepins

1985 ◽  
Vol 50 (5) ◽  
pp. 1078-1088 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
Miroslav Protiva
Keyword(s):  
Hydrochloric Acid ◽  
Ir Spectrum ◽  
Title Compound ◽  
Dilute Hydrochloric Acid ◽  
Amino Alcohols ◽  
Geometric Isomers ◽  
Pharmacological Testing

Reaction of dibenzo[b,e]thiepin-11(6H)-one with 2-(dimethylaminomethyl)cyclohexylmagnesium chloride gave a mixture of stereoisomeric amino alcohols IX from which four homogeneous bases (IXa to IXd) were separated by chromatography. Dehydration of these compounds with boiling dilute hydrochloric acid afforded mixtures of racemic geometric isomers of the title compound VII, which were separated by crystallization. To the prevailing less polar base VIIa (E)-configuration was assigned on the basis of the IR spectrum. Using a similar procedure, thieno[2,3-c]-2-benzothiepin-4(9H)-one gave mixture of amino alcohols X from which three homogeneous stereoisomers X-A to X-C were isolated. Their dehydration resulted in both expected racemic geometric isomers VIII-A and VIII-B. Pharmacological testing proved the character of an antidepressant for the semi-rigid analogue of dithiadene VIII.

scholarly journals Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes

2021 ◽  
Author(s):  
Eryn Nelson ◽  
Jeffrey S. S. K. Formen ◽  
Christian Wolf
Keyword(s):  
Amino Acids ◽  
Absolute Configuration ◽  
Rapid Determination ◽  
Amino Alcohols ◽  
Enantioselective Synthesis ◽  
Widespread Occurrence ◽  
Chiral Compounds ◽  
New Methods ◽  
The Absolute

The widespread occurrence and significance of chiral compounds does not only require new methods for their enantioselective synthesis but also efficient tools that allow rapid determination of the absolute configuration,...

scholarly journals Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3223
Author(s):  
Ji-Wei Zhang ◽  
Shao-Hua Xiang ◽  
Shaoyu Li ◽  
Bin Tan
Keyword(s):  
Amino Alcohols ◽  
Sigmatropic Rearrangement ◽  
Synthetic Route ◽  
Mild Conditions ◽  
Good Substrate ◽  
Diaryliodonium Salts ◽  
Axially Chiral

NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols.

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