TY - JOUR
T1 - Exploring the synthesis of deceptively simple Biginelli products through N-CN bond cleavage
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
N1 - Publisher Copyright:
© 2016 The Japan Institute of Heterocyclic Chemistry Received.
PY - 2016
Y1 - 2016
N2 - 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 - 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.
UR - http://www.scopus.com/inward/record.url?scp=84992695495&partnerID=8YFLogxK
U2 - 10.3987/COM-16-13524
DO - 10.3987/COM-16-13524
M3 - Artículo
SN - 0385-5414
VL - 92
SP - 1803
EP - 1809
JO - Heterocycles
JF - Heterocycles
IS - 10
ER -