About: Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives

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About: Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
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 stability of 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. 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 stability of 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. (en) 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 stability of 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. (cs)
Title	Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives (en) Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives (cs)
skos:prefLabel	Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives (en) Theoretical Confirmation of the Reaction Mechanism Leading to Regioselective Formation of Thiazolidin-4-one from Bromoacetic Acid Derivatives (cs)
skos:notation	RIV/60461373:22340/07:00019336!RIV08-MSM-22340___
http://linked.open.../vavai/riv/strany	1435-1445
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM6046137301)
http://linked.open...iv/cisloPeriodika	10
http://linked.open...vai/riv/dodaniDat	2008
http://linked.open...aciTvurceVysledku	Böhm, Stanislav
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta chemicko-inženýrská
http://linked.open...dnocenehoVysledku	454994
http://linked.open...ai/riv/idVysledku	RIV/60461373:22340/07:00019336
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	B3LYP functional; Bromoacetic acid; DFT calculations; Reaction mechanisms; Regioselectivity; Thiourea; Thiazolidinone. (en)
http://linked.open.../riv/klicoveSlovo	Regioselectivity Reaction mechanisms Thiourea DFT calculations B3LYP functional Bromoacetic acid Thiazolidinone.
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[A541EB532647]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...UplatneniVysledku	2007
http://linked.open...v/svazekPeriodika	72
http://linked.open...iv/tvurceVysledku	Böhm, Stanislav Janovec, Ladislav Imrich, Jan Kristian, Pavol Danihel, Ivan Klika, Karel
http://linked.open...n/vavai/riv/zamer	Catalytic processes in chemistry and chemical technology
issn	0010-0765
number of pages	11 (xsd:int)
http://localhost/t...ganizacniJednotka	22340

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