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Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives: new synthetic routes and crystal structures

MPG-Autoren
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Engelmann,  J
Department High-Field Magnetic Resonance, Max Planck Institute for Biological Cybernetics, Max Planck Society;
Max Planck Institute for Biological Cybernetics, Max Planck Society;

Externe Ressourcen

https://www.sciencedirect.com/science/article/pii/S0040402011018618
(Verlagsversion)

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Zitation

Mallah, E., Sweidan, K., Engelmann, J., Steimann, M., Kuhn, N., & Maier, M. (2012). Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives: new synthetic routes and crystal structures. Tetrahedron, 68(4), 1005-1010. doi:10.1016/j.tet.2011.11.093.


Zitierlink: https://hdl.handle.net/21.11116/0000-0001-8A88-A
Zusammenfassung
We describe simple, convenient and high-yielding nucleophilic substitution reactions to synthesize new derivatives of 1,3-dimethylbarbituric acid (1a). Based on its active C5 position, condensing 1a with sulfuryl chloride gives the corresponding 5,5-dichloro-1,3-dimethylbarbituric acid (13). The latter was reacted with silver nitrite and potassium cyanide to afford 5-chloro-5-nitro-1,3-dimethylbarbituric acid (14) and 5-cyano-1,3-dimethylbarbiturate (17), respectively. Furthermore, by employing the nucleophilic character of 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (8) the obtained compounds 13 and 14 have been converted to 2-chloro-1,3-diisopropyl-4,5-dimethyl-1H-imidazol-3-ium-1,3-dimethyl-5-nitro-1,3-dimethylbarbiturate (18) and 1,3-dimethylbarbituric acid trimer (21), respectively. X-ray structures for compounds 13, 14, 17, 18 and 21 were determined.