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, Francisco Delgado

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

© 2016 The Japan Institute of Heterocyclic Chemistry Received. 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.
Original languageAmerican English
Pages (from-to)1803-1809
Number of pages1622
JournalHeterocycles
DOIs
StatePublished - 1 Jan 2016

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formic acid
Acids
Japan
Atoms
pyrimidine
dicyandiamido

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Fidencio, J. J. N., Ríos-Guerra, H., González-Villanueva, G., Penieres-Carrillo, J. G., Balcázar, G. G., Nicolás-Vázquez, M. I., & Delgado, F. (2016). Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage. Heterocycles, 1803-1809. https://doi.org/10.3987/COM-16-13524
Fidencio, Juan Jesús Nolasco ; Ríos-Guerra, Hulme ; González-Villanueva, Gilberto ; Penieres-Carrillo, José Guillermo ; Balcázar, Gustavo Guevara ; Nicolás-Vázquez, Ma Inés ; Delgado, Francisco. / Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage. In: Heterocycles. 2016 ; pp. 1803-1809.
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Fidencio, JJN, Ríos-Guerra, H, González-Villanueva, G, Penieres-Carrillo, JG, Balcázar, GG, Nicolás-Vázquez, MI & Delgado, F 2016, 'Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage', Heterocycles, pp. 1803-1809. https://doi.org/10.3987/COM-16-13524

Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage. / Fidencio, Juan Jesús Nolasco; Ríos-Guerra, Hulme; González-Villanueva, Gilberto; Penieres-Carrillo, José Guillermo; Balcázar, Gustavo Guevara; Nicolás-Vázquez, Ma Inés; Delgado, Francisco.

In: Heterocycles, 01.01.2016, p. 1803-1809.

Research output: Contribution to journalArticle

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AU - Fidencio, Juan Jesús Nolasco

AU - Ríos-Guerra, Hulme

AU - González-Villanueva, Gilberto

AU - Penieres-Carrillo, José Guillermo

AU - Balcázar, Gustavo Guevara

AU - Nicolás-Vázquez, Ma Inés

AU - Delgado, Francisco

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N2 - © 2016 The Japan Institute of Heterocyclic Chemistry Received. 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.

AB - © 2016 The Japan Institute of Heterocyclic Chemistry Received. 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.

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Fidencio JJN, Ríos-Guerra H, González-Villanueva G, Penieres-Carrillo JG, Balcázar GG, Nicolás-Vázquez MI et al. Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage. Heterocycles. 2016 Jan 1;1803-1809. https://doi.org/10.3987/COM-16-13524