About: The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil

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About: The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The mechanism of the decomposition of acryloylcarbamates yielding highly reactive isocyanates was proposed based on NMR measurements and quantum chemical calculations. A good agreement between the experimental kinetic data and DFT calculations allowed us to demonstrate that the stability of 7a-d depends on the presence ofmethyl in the acryloylmoiety and the position of the nitro group in the nitrophenolic part of themolecule. Furthermore, the reactivity of these reagents with weakly nucleophilic and sterically hindered 2,4,6-tri-tert-butylaniline was explored by 1H NMR demonstrating the usefulness of reagents 7a-d offering access to a variety of 1-N-substituted uracils and thymines with potentially interesting biological properties. The mechanism of the decomposition of acryloylcarbamates yielding highly reactive isocyanates was proposed based on NMR measurements and quantum chemical calculations. A good agreement between the experimental kinetic data and DFT calculations allowed us to demonstrate that the stability of 7a-d depends on the presence ofmethyl in the acryloylmoiety and the position of the nitro group in the nitrophenolic part of themolecule. Furthermore, the reactivity of these reagents with weakly nucleophilic and sterically hindered 2,4,6-tri-tert-butylaniline was explored by 1H NMR demonstrating the usefulness of reagents 7a-d offering access to a variety of 1-N-substituted uracils and thymines with potentially interesting biological properties. (en)
Title	The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study (en)
skos:prefLabel	The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study (en)
skos:notation	RIV/61388963:_____/11:00359404!RIV12-AV0-61388963
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(2B06065), P(LC512), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Rulíšek, Lubomír Pohl, Radek Rejman, Dominik
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	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	231841
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/11:00359404
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	mechanism; NMR; nucleosidation (en)
http://linked.open.../riv/klicoveSlovo	nucleosidation NMR mechanism
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[F63CF493BDDD]
http://linked.open...i/riv/nazevZdroje	Journal of Physical Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...vavai/riv/projekt	New Generation of Antibacterial Agens Center for biomolecules and complex molecular systems
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	24
http://linked.open...iv/tvurceVysledku	Pohl, Radek Rulíšek, Lubomír Rejman, Dominik
http://linked.open...ain/vavai/riv/wos	000290360500009
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	0894-3230
number of pages	8 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/poc.1775

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