Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4- ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study
Result description
Acridine thiosemicarbazones 3aeg, obtained through a two-step reaction between aromatic isothiocyanates and hydrazine followed by the treatment with acridin-9-carbaldehyde, in reaction with bifunctional reagents; methyl bromoacetate (MBA) and diethyl acetylenedicarboxylate (DEAD) afforded acridin-thiazolidinone derivatives 4aeg and 7aef and not their regioisomers 6aeg and 9aef. Derivatives 4aeg and 7aef exhibit ZC2N6EN7C8 configuration. Upon standing in DMSO-d6 the thiazolidinones 4aeg and 7aef spontaneously isomerized into ZC2N6ZN7C8 isomers 5aeg and 8aef to give a mixture of the both stereoisomers. All compounds were fully characterized by multinuclear NMR, mass spectrometry (MS) and X-ray crystal structure of 4b is also described. X-ray diffraction study revealed that the representative compound 4b crystallized in the monoclinic crystal system with the C2/c space group and Z ¼ 4. Intramolecular C10eH10/N-7 hydrogen bond between the acridine proton H-10 and nitrogen N-7 of linker existed. This hydrogen bond is responsible for the E isomerism on C-8 atom which was observed in the NMR experiments. Quantum-chemical calculations and NOESY experiments confirmed ZC2N6ZN7C8 configuration of the transformed stereoisomers 5aeg and 8aef.
Keywords
AcridineThiazolidinoneE/Z isomerNMR spectroscopySingle crystal X-ray study
The result's identifiers
Result code in IS VaVaI
Result on the web
https://www.sciencedirect.com/science/article/pii/S0022286017313893
DOI - Digital Object Identifier
Alternative languages
Result language
angličtina
Original language name
Synthesis and isomerization of acridine substituted 1,3-thiazolidin-4- ones and 4-oxo-1,3-thiazolidin-5-ylidene acetates. An experimental and computational study
Original language description
Acridine thiosemicarbazones 3aeg, obtained through a two-step reaction between aromatic isothiocyanates and hydrazine followed by the treatment with acridin-9-carbaldehyde, in reaction with bifunctional reagents; methyl bromoacetate (MBA) and diethyl acetylenedicarboxylate (DEAD) afforded acridin-thiazolidinone derivatives 4aeg and 7aef and not their regioisomers 6aeg and 9aef. Derivatives 4aeg and 7aef exhibit ZC2N6EN7C8 configuration. Upon standing in DMSO-d6 the thiazolidinones 4aeg and 7aef spontaneously isomerized into ZC2N6ZN7C8 isomers 5aeg and 8aef to give a mixture of the both stereoisomers. All compounds were fully characterized by multinuclear NMR, mass spectrometry (MS) and X-ray crystal structure of 4b is also described. X-ray diffraction study revealed that the representative compound 4b crystallized in the monoclinic crystal system with the C2/c space group and Z ¼ 4. Intramolecular C10eH10/N-7 hydrogen bond between the acridine proton H-10 and nitrogen N-7 of linker existed. This hydrogen bond is responsible for the E isomerism on C-8 atom which was observed in the NMR experiments. Quantum-chemical calculations and NOESY experiments confirmed ZC2N6ZN7C8 configuration of the transformed stereoisomers 5aeg and 8aef.
Czech name
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Czech description
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Classification
Type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
LO1204: Sustainable development of research in the Centre of the Region Haná
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
JOURNAL OF MOLECULAR STRUCTURE
ISSN
0022-2860
e-ISSN
—
Volume of the periodical
1154
Issue of the periodical within the volume
FEB
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
13
Pages from-to
152-164
UT code for WoS article
000418212000019
EID of the result in the Scopus database
2-s2.0-85031714368
Basic information
Result type
Jimp - Article in a specialist periodical, which is included in the Web of Science database
OECD FORD
Physical chemistry
Year of implementation
2018