A cascade reaction with iminium ion isomerization as the key step leading to tetrahydropyrimido[4,5-d]pyrimidines.
A novel cascade reaction of aminopyrimidines 1 with N-alkyl amino acids or analogues was investigated. The keys to this cascade are the isomerization of an iminium ion formed between the aldehyde group in pyrimidine and the secondary amine of an amino acid, and subsequent cyclization to the neighboring amino group. This sequence could be useful in the synthesis of novel tetrahydropyrimido[4,5-d]pyrimidine libraries.
Zheng
Lianyou
L
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai Street, Changchun, Jilin 130012, People's Republic of China.
Yang
Fengzhi
F
Dang
Qun
Q
Bai
Xu
X
D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007097:Imines; D011743:Pyrimidines