Ninhydrin Revisited: Quantitative Chirality Recognition of Amines and Amino Alcohols Based on Nondestructive Dynamic Covalent Chemistry

2020 ◽  
Vol 85 (17) ◽  
pp. 11560-11565
Author(s):  
Samantha L. Pilicer ◽  
Christian Wolf
Keyword(s):  
Amino Alcohols ◽  
Dynamic Covalent Chemistry

Formation and Trapping of the Thermodynamically Unfavoured Inverted-Hemicucurbit[6]uril

2019 ◽  
Author(s):  
Elena Prigorchenko ◽  
Sandra Kaabel ◽  
Triin Narva ◽  
Anastassia Baškir ◽  
Maria Fomitšenko ◽  
...  
Keyword(s):  
Complex Formation ◽  
Combinatorial Chemistry ◽  
Trifluoroacetic Acid ◽  
Chloride Anion ◽  
Binding Affinities ◽  
Dynamic Covalent Chemistry ◽  
Reaction Selectivity ◽  
Low Concentration ◽  
Dynamic Combinatorial Chemistry ◽  
First Time

Amplification of a thermodynamically unfavoured macrocyclic product through the directed shift of the equilibrium between dynamic covalent chemistry library members is difficult to achieve. We show for the first time that during condensation of formaldehyde and <i>cis</i>-<i>N,N'</i>-cyclohexa-1,2-diylurea formation of <i>inverted-cis</i>-cyclohexanohemicucurbit[6]uril (<i>i-cis</i>-cycHC[6]) can be induced at the expense of thermodynamically favoured <i>cis</i>-cyclohexanohemicucurbit[6]uril (<i>cis</i>-cycHC[6]). The formation of <i>i-cis-</i>cycHC[6] is enhanced in low concentration of the templating chloride anion and suppressed in excess of this template. We found that reaction selectivity is governed by the solution-based template-aided dynamic combinatorial chemistry and continuous removal of the formed cycHC[6] macrocycles from the equilibrating solution by precipitation. Notably, the <i>i-cis</i>-cycHC[6] was isolated with 33% yield. Different binding affinities of three diastereomeric <i>i-cis</i>-, <i>cis</i>-cycHC[6] and their chiral isomer (<i>R,R</i>)-cycHC[6] for trifluoroacetic acid demonstrate the influence of macrocycle geometry on complex formation.

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.

Sign in / Sign up

Export Citation Format

Share Document