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Synthesis 2018; 50(20): 4071-4080
DOI: 10.1055/s-0037-1609576
DOI: 10.1055/s-0037-1609576
paper
Preparation and Reactions of Trichloromethyl-Substituted Pyridine and Pyrimidine Derivatives
This work was funded by the Deutsche Forschungsgemeinschaft.This work was generously supported by Bayer HealthCare.
Further Information
Publication History
Received: 04 June 2018
Accepted after revision: 20 June 2018
Publication Date:
17 July 2018 (online)
Abstract
The three-component reaction of lithiated methoxyallene, nitriles and trichloroacetic acid gave three model β-keto enamides that were starting materials for the synthesis of trichloromethyl-substituted pyridine and pyrimidine N-oxide derivatives. Upon treatment with acetic anhydride, the methyl group of the prepared pyrimidine N-oxides was converted into an acetoxymethyl group by a Boekelheide rearrangement. A few typical experiments also revealed that the trichloromethyl group of the prepared pyrimidine N-oxides can be replaced by an alkoxy or a hydroxy group, or transformed into an arylthiomethyl group. An alternative approach to β-keto enamides via the corresponding β-keto enamines was also examined and provided the expected 4-hydroxy-6-(trichloromethyl)pyridine derivative in good yield.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609576.
- Supporting Information
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