Cyanamide: a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction

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• 作者：R. Hulme ; O.D.P. Zamora ; E.J. Mota ; M.A. Pasté ; n ; R. Contreras-Rojas ; R. Mir ; a ; I. Valencia-Herná ; ndez ; J. Correa-Basurto ; J. Trujillo-Ferrara ; F. Delgado
• 关键词：Cyanamide ; Building block ; Multicomponent reaction ; 4-Aryl-2-cyanoimino-3 ; 4-dihydro-1H-pyrimidine
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：7 April 2008
• 年：2008
• 卷：64
• 期：15
• 页码：3372-3380
• 全文大小：341 K

文摘

4-Aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine derivatives were prepared using a multicomponent reaction by reacting a mixture of arene or heteroarenecarbaldehyde, 1,3-dicarbonyl compounds, and cyanamide under acidic conditions. The novelty of this approach derives from its use of cyanamide as a building block in a four-component Biginelli-type reaction. Varying the reaction conditions led to the formation of either N-(2-imino-6-phenyl-1,3,5-oxadiazinan-4-ylidene) cyanamide or 3,4-dihydropyrimidin-2(1H)-one. The type of heterocycle skeleton synthesized depends on the nature of the acid catalyst as well as the reaction conditions employed.