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The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - an NMR and DFT study
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SYSNO ASEP 0359404 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS 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 Author(s) Pohl, Radek (UOCHB-X) RID, ORCID
Rulíšek, Lubomír (UOCHB-X) RID, ORCID
Rejman, Dominik (UOCHB-X) RID, ORCIDNumber of authors 3 Source Title Journal of Physical Organic Chemistry. - : Wiley - ISSN 0894-3230
Roč. 24, č. 5 (2011), s. 423-430Number of pages 8 s. Language eng - English Country GB - United Kingdom Keywords mechanism ; NMR ; nucleosidation Subject RIV CC - Organic Chemistry R&D Projects 2B06065 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000290360500009 DOI 10.1002/poc.1775 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2012
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