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Unexpected Reaction Products of Uracil and Its Methyl Derivatives with Acetic Anhydride and Methylene Chloride

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cris.lastimport.scopus2024-02-12T20:05:57Z
dc.abstract.enNew acetyl derivatives of uracil, 6-methyluracil, and thymine were obtained in the course of an unconventional synthesis in methylene chloride. It was shown that products with the acetyloxymethyl fragment are formed according to a mechanism different from that for products with the acetyloxyethyl group. In particular, for uracil it was proven that the reaction with Ac2O, TEA, and CH2Cl2 leads to 1-acetyloxymethyluracil, where the N1 substituent is composed of the −CH2− fragment that originated from CH2Cl2 and the 1-acetyloxy moiety from Ac2O. The reaction of uracil with Ac2O, TEA, CH2Cl2, and DMAP leads to an acetyloxyethyl derivative in which the −CH2−CH2− fragment originates from TEA and the 1-acetyloxy moiety from Ac2O. A possible mechanism for the formation of new compounds was suggested and supported by the density functional theory/B3LYP quantum mechanical calculations. New compounds (39 in total, including seven deuterated) were fully characterized by nuclear magnetic resonance and high-resolution mass spectrometry techniques .
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCybulski, Marcin
dc.contributor.authorTrzcińska, Kinga
dc.contributor.authorKrzeczyński, Piotr
dc.contributor.authorCmoch, Piotr
dc.contributor.authorMichalak, Olga
dc.contributor.authorLEŚ, ANDRZEJ
dc.contributor.authorMiszta, Przemysław
dc.contributor.authorFilipek, Sławomir
dc.contributor.authorJain, Pakhuri
dc.date.accessioned2024-01-26T11:19:14Z
dc.date.available2024-01-26T11:19:14Z
dc.date.issued2021
dc.description.financePublikacja bezkosztowa
dc.description.number21
dc.description.volume86
dc.identifier.doi10.1021/ACS.JOC.1C00748
dc.identifier.issn0022-3263
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/124175
dc.identifier.weblinkhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.1c00748
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.pages14321–14332
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleUnexpected Reaction Products of Uracil and Its Methyl Derivatives with Acetic Anhydride and Methylene Chloride
dc.typeJournalArticle
dspace.entity.typePublication