Issue 2, 2019
From the journal:

Organic & Biomolecular Chemistry

A diversity of alkylation/acylation products of uracil and its derivatives: synthesis and a structural study†

Olga Michalak, ORCID logo *a   Piotr Cmoch,b   Piotr Krzeczyński,a   Marcin Cybulskia  and  Andrzej Leśac  

* Corresponding authors

a Pharmaceutical Research Institute, 8 Rydygiera Str., 01-793 Warsaw, Poland
E-mail: o.michalak@ifarm.eu
Tel: +48 22 456 3925

b Institute of Organic Chemistry Polish Academy of Sciences, 44/52 Kasprzaka street, 01-224 Warsaw, Poland

c University of Warsaw, Faculty of Chemistry, 1 Pasteura Str., 02-093 Warsaw, Poland

Abstract

tert-Butyl dicarbonate (Boc2O) and ethyl iodide (EtI) reactions with uracil (U), thymine (T) and 6-methyluracil (6-MU) were performed following routine procedures in pyridine/DMF solvents and with DMAP as the catalyst. Among 20 synthesized compounds, a derivative of 6-methyluracil substituted by the Boc-pyridine moiety at the C5 position appeared unexpectedly. The NMR spectra confirmed the molecular structure of all uracil derivatives. Parallel quantum mechanical DFT calculations supported the experimental findings.

Graphical abstract: A diversity of alkylation/acylation products of uracil and its derivatives: synthesis and a structural study

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Article information

DOI
https://doi.org/10.1039/C8OB02552E
Article type
Paper
Submitted
15 Oct 2018
Accepted
10 Dec 2018
First published
10 Dec 2018

Org. Biomol. Chem., 2019,17, 354-362

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A diversity of alkylation/acylation products of uracil and its derivatives: synthesis and a structural study

O. Michalak, P. Cmoch, P. Krzeczyński, M. Cybulski and A. Leś, Org. Biomol. Chem., 2019, 17, 354 DOI: 10.1039/C8OB02552E

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