Synthesis of 2,4-dibenzoyloxy-6-methylpyrimidine and its acylotropic transformations

Podzigun, G. I.; Petrova, Veselina; Резник, В. С.; Schagidullin, R. R.; Avvakumova, L. V.

doi:10.1007/bf02494388

Cited by 2 publications

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“…Leslie and Secco determined the structure of the N 1 -acetylthymine crystal, whereas Güney et al obtained a derivative of N 1 -acetyluracil in the reaction of uracil with acetic anhydride, in pyridine as the solvent and base. Podzigun et al proved that, unlike uracil and thymine, 6-methyluracil is not acetylated by acetic anhydride (140 °C, pyridine) …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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New 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 N 1 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.

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Section: Introductionmentioning

confidence: 99%

“…Podzigun et al proved that, unlike uracil and thymine, 6-methyluracil is not acetylated by acetic anhydride (140 °C, pyridine). 14 In light of literature data, it was necessary to develop a new method for the synthesis of 6-methyluracil acetyl derivatives. We have studied various reaction routes, changing both solvents and bases.…”

Section: ■ Introductionmentioning

confidence: 99%