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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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| Authors: | R Hulme ODP Zamora MA Pastén R Miranda J Correa-Basurto F Delgado |
| Institution: | a Departamento de Ciencias Quimicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Avenida 1ro de Mayo s/n, Cuautitlán Izcalli, Estado de México, CP 54740, Mexico b Escuela Superior de Medicina-IPN, Plan de San Luis y Díaz Mirón, Col. Santo Tomás, México, D.F., CP 11340, Mexico c Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación Carpio y Plan de Ayala, Casco de Santo Tomás, México, D.F., CP 11340, Mexico |
| Abstract: | 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. |
| Keywords: | Cyanamide Building block Multicomponent reaction 4-Aryl-2-cyanoimino-3 4-dihydro-1H-pyrimidine |
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