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Paper | Regular issue | Vol 92, No. 10, 2016, pp.1803-1809
Published online, 6th September, 2016
DOI: 10.3987/COM-16-13524
Exploring the Synthesis of Deceptively Simple Biginelli Products through N-CN Bond Cleavage

Juan Jesús Nolasco Fidencio, Hulme Ríos-Guerra,* Gilberto González-Villanueva, José Guillermo Penieres-Carrillo, Gustavo Guevara Balcázar, Ma. Inés Nicolás-Vázquez, Hulme Ríos-Guerra, and Francisco Delgado

*Faculty of Higher Cuautitlan Studies, Chemistry Science Department, UNAM, Av. 1° de Mayo s/n Sta. Ma. Gpe. las Torres, Postcode 54740, Cuautitlán Izcalli, Mexico

Abstract

Brønsted-Lowry acid-promoted cleavage of the N-CN bond in 2-cyanoimino-3,4-dihydro-(1H)-pyrimidine is described. Formic acid efficiently activates cyclic N-cyanoguanidines through an O-formylisourea reactive intermediate, leading to chemospecific N-CN bond cleavage of the cyanoimine moiety. This low environmental-load method provides step- and atom-economical access to difficult-to-obtain acid-sensitive Biginelli products in excellent yields.