A cascade reaction consisting of Pictet-Spengler-type cyclization and Smiles rearrangement: application to the synthesis of novel pyrrole-fused dihydropteridines.
[reaction: see text] Tandem Pictet-Spengler-type cyclization and Smiles rearrangement have been discovered in the synthesis of pyrimidine-fused heterocycles. The reaction of 4-chloro-5-pyrrol-1-ylpyrimidine amino aldehyde with an amine under an acidic condition yielded the Pictet-Spengler-type cyclization product diazepine, which readily underwent Smiles rearrangement to give a novel pyrrolo[1,2-f]pteridine derivative.
Xiang
Jinbao
J
The Center for Combinatorial Chemistry and Drug Discovery, Jilin University, 75 Haiwai Street, Changchun, Jilin 130012, P. R. China.
Zheng
Lianyou
L
Chen
Feng
F
Dang
Qun
Q
Bai
Xu
X
D018360:Crystallography, X-Ray; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011621:Pteridines / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D011621:Pteridines; D011758:Pyrroles; D006859:Hydrogen