Reaction of Tertiary 2‐Chloroketones with Cyanide Ions: Application to 3‐Chloroquinolinediones
| Autor: | Antonín Lyčka, Antonín Klásek, Stanislav Kafka, Michal Rouchal, Lukáš Bednář, Ondřej Rudolf |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
α-cyanooxiranes
Cyanohydrin reaction Cyanide Substituent α-Cyanooxiranes Epoxide solvent effects 010402 general chemistry 01 natural sciences Medicinal chemistry cyanohydrin reaction chemistry.chemical_compound Solvent effects QD1-999 Cyanides Full Paper 010405 organic chemistry cyanides α-haloketones General Chemistry Full Papers 0104 chemical sciences NMR spectra database α-Haloketones Chemistry chemistry Methanol Methyl group |
| Zdroj: | ChemistryOpen, Vol 10, Iss 6, Pp 645-652 (2021) ChemistryOpen |
| ISSN: | 2191-1363 |
| Popis: | 3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position is the methyl group. In the methanol solution, the reaction proceeds by an addition mechanism to form 2-oxo-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-7b-carbonitriles, from which 4-hydroxy-3-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-4-carbonitriles are subsequently formed by opening of the epoxide ring with methanol. Some minor products of these reactions have also been isolated. The 1 H, 13 C and 15 N NMR spectra of the prepared compounds were measured, and all resonances were assigned using appropriate two-dimensional spectra. © 2021 The Authors. Published by Wiley-VCH GmbH. Tomas Bata University in Zlin [IGA/FT/2020/007] Funding Source: Medline Univerzita Tomáše Bati ve Zlíně: IGA/FT/2020/007 |
| Databáze: | OpenAIRE |
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