Acyl pyruvates as synthons in the Biginelli reaction

作者：Ryabukhin Sergey V^*; Plaskon Andrey S; Bondarenko Semen S; Ostapchuk Eugeniy N; Grygorenko Oleksandr O; Shishkin Oleg V; Tolmachev Andrey A

来源：Tetrahedron Letters, 2010, 51(32): 4229-4232.

DOI：10.1016/j.tetlet.2010.06.032

• Multicomponent reactions
• Heterocycles
• Biginelli reaction
• Dihydropyrimidines
• Acyl pyruvates

Chlorotrimethylsilane-promoted Biginelli-type reaction of ethyl 2,4-dioxo-4-phenylbutanoate, benzaldehyde, and various (thio)ureas is explored. The outcome of the reaction depends on the structure of the (thio)urea used and is strongly affected by the acceptor electronic properties of the COOEt substituent in the molecule of the starting beta-dicarbonyl compound. The di- and tetrahydropyrimidine derivatives obtained possess two functional groups with orthogonal reactivity, and thus represent promising building blocks for drug discovery.

• 出版日期2010-8-11