Tetrahedron

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

E Mallah, K Sweidan, J Engelmann, M Steimann…

Index: Mallah, Eyad; Sweidan, Kamal; Engelmann, Joern; Steimann, Manfred; Kuhn, Norbert; Maier, Martin E. Tetrahedron, 2012 , vol. 68, # 4 p. 1005 - 1010

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Citation Number: 5

Abstract

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- ...