Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F07%3A00019336" target="_blank" >RIV/60461373:22340/07:00019336 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives
Original language description
A regioselective synthesis of 3-alkyl-2-[(anthracen-9-yl)imino]thiazolidin-4-ones 2a-2e and 2-(alkylimino)-3-(anthracen-9-yl)thiazolidin-4-ones 3a-3e from appropriate thioureas using methyl bromoacetate or bromoacetyl bromide, respectively, has been rationalized by DFT calculations of model thiourea and its phenyl derivative. The proposed mechanism indicates that the regioselective formation of the target thiazolidinones is a consequence of a different reactivity of the reagents and a varying stabilityof the intermediates, 1-alkyl-3-(anthracen-9-yl)-2-[(methoxycarbonyl)methyl]isothioureas 4a-4e and 1-alkyl-3-(anthracen-9-yl)-2-(bromoacetyl)isothioureas 6a-6e.
Czech name
Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives
Czech description
A regioselective synthesis of 3-alkyl-2-[(anthracen-9-yl)imino]thiazolidin-4-ones 2a-2e and 2-(alkylimino)-3-(anthracen-9-yl)thiazolidin-4-ones 3a-3e from appropriate thioureas using methyl bromoacetate or bromoacetyl bromide, respectively, has been rationalized by DFT calculations of model thiourea and its phenyl derivative. The proposed mechanism indicates that the regioselective formation of the target thiazolidinones is a consequence of a different reactivity of the reagents and a varying stabilityof the intermediates, 1-alkyl-3-(anthracen-9-yl)-2-[(methoxycarbonyl)methyl]isothioureas 4a-4e and 1-alkyl-3-(anthracen-9-yl)-2-(bromoacetyl)isothioureas 6a-6e.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2007
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Collection of Czechoslovak Chemical Communications
ISSN
0010-0765
e-ISSN
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Volume of the periodical
72
Issue of the periodical within the volume
10
Country of publishing house
CZ - CZECH REPUBLIC
Number of pages
11
Pages from-to
1435-1445
UT code for WoS article
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EID of the result in the Scopus database
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