Highly diastereoselective domino synthesis of 6-spirosubstituted pyrido[2,3-d]pyrimidine derivatives in water.
A highly diastereoselective domino reaction of 2,6-diaminopyrimidine-4-one with structurally diverse aryl aldehydes and various barbituric acids in water under microwave irradiation is described. The products are 6-spiro-substituted pyrido[2,3-d]pyrimidines with high diastereoselectivities (up to 99: 1) in which the major diastereomer bears a cis relationship between substituents at the 5- and 7-positions. Furthermore, the mechanism for diastereoselectivity was confirmed by DFT (B3LYP) calculations.
Jiang
Bo
B
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, P. R. China.
Cao
Long-Ji
LJ
Tu
Shu-Jiang
SJ
Zheng
Wen-Rui
WR
Yu
Hai-Zhu
HZ
D000447:Aldehydes / Q000737:chemistry; D001463:Barbiturates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D008872:Microwaves; D008958:Models, Molecular; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000447:Aldehydes; D001463:Barbiturates; D011743:Pyrimidines; D013141:Spiro Compounds; D014867:Water; C032232:barbituric acid