Microwave-assisted combinatorial synthesis of new 3-pyrimidin-5-ylpropanamides via a solvent-dependent chemoselective reaction.
A series of new 3-pyrimidin-5-ylpropanamides was selectively synthesized via a microwave-assisted, chemoselective reaction of arylidene-Meldrum's acid, 6-hydroxypyrimidin-4(3H)-one, and structurally diverse amines including (S or R)-1-phenylethanamine, cyclohexanamine, and cyclopentanamine depended on nature of solvents. In this reaction, the utilization of HOAc as a solvent leads to 3-pyrimidin-5-ylpropanamides, whereas water as reaction media results in the spiro[5.5]undecane-1,5,9-triones from same starting materials. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environment impact.
Hao
Wen-Juan
WJ
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou, Jiangsu 221116, PR China.
Jiang
Bo
B
Tu
Shu-Jiang
SJ
Wu
Shan-Shan
SS
Han
Zheng-Guo
ZG
Cao
Xu-Dong
XD
Zhang
Xiao-Hong
XH
Yan
Shu
S
Shi
Feng
F
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D008872:Microwaves; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents / Q000737:chemistry
C552174:3-pyrimidin-5-ylpropanamide; D000577:Amides; D011743:Pyrimidines; D012997:Solvents