TY - JOUR
T1 - Cyanamide
T2 - a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction
AU - Hulme, R.
AU - Zamora, O. D.P.
AU - Mota, E. J.
AU - Pastén, M. A.
AU - Contreras-Rojas, R.
AU - Miranda, R.
AU - Valencia-Hernández, I.
AU - Correa-Basurto, J.
AU - Trujillo-Ferrara, J.
AU - Delgado, F.
N1 - Funding Information:
F.D. would like to acknowledge CONACyT (Grant 44038-Q) and SIP/IPN (Grant 20060055, 20070617) for financial support. R.H. is grateful to CONACyT for a graduate scholarship and a Research Fellowship IN1-69, FESC-UNAM. I.V.-H. is a fellow of the EDI/IPN and COFAA/IPN programs. The authors are grateful to Ms. Ana P. Contreras Rojas (McGill University, Montreal Canada) for reviewing the manuscript.
PY - 2008/4/7
Y1 - 2008/4/7
N2 - 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.
AB - 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.
KW - 4-Aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine
KW - Building block
KW - Cyanamide
KW - Multicomponent reaction
UR - http://www.scopus.com/inward/record.url?scp=39749141493&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.01.087
DO - 10.1016/j.tet.2008.01.087
M3 - Artículo
SN - 0040-4020
VL - 64
SP - 3372
EP - 3380
JO - Tetrahedron
JF - Tetrahedron
IS - 15
ER -