1. Unexpected Reaction Products of Uracil and Its Methyl Derivatives with Acetic Anhydride and Methylene Chloride.
- Author
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Michalak O, Cmoch P, Leś A, Cybulski M, Krzeczyński P, Trzcińska K, Miszta P, Mehta P, and Filipek S
- Subjects
- Acetic Anhydrides, Thymine, Methylene Chloride, Uracil
- Abstract
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 Ac
2 O, TEA, and CH2 Cl2 leads to 1-acetyloxymethyluracil, where the N1 substituent is composed of the -CH2 - fragment that originated from CH2 Cl2 and the 1-acetyloxy moiety from Ac2 O. The reaction of uracil with Ac2 O, TEA, CH2 Cl2 , and DMAP leads to an acetyloxyethyl derivative in which the -CH2 -CH2 - fragment originates from TEA and the 1-acetyloxy moiety from Ac2 O. 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.- Published
- 2021
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