One-pot synthesis of quinoline-based tetracycles by a tandem three-component reaction.
A practical one-pot synthetic strategy for the efficient synthesis of a range of structurally interesting and bioactive quinoline-based tetracycles has been developed. A key step in the synthesis is a tandem three-component reaction of heteroaromatic amine, methyl 2-formylbenzoate and (t)butyl isonitrile, followed by TFA-mediated lactamization via intramolecular aminolysis of an adjacent ester. Results related to a kinase-panel screening for several selected compounds are also discussed in this article.
Che
Chao
C
Laboratory of Chemical Genomics, Shenzhen Graduate School, Peking University, Beijing, 100871.
Xiang
Jing
J
Wang
Guo-Xin
GX
Fathi
Reza
R
Quan
Jun-Min
JM
Yang
Zhen
Z
D000588:Amines / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry; D010770:Phosphotransferases / Q000037:antagonists & inhibitors / Q000378:metabolism; D011804:Quinolines / Q000138:chemical synthesis*
D000588:Amines; D001565:Benzoates; D004952:Esters; D006576:Heterocyclic Compounds, 4 or More Rings; D007769:Lactams; D009570:Nitriles; D011804:Quinolines; D010770:Phosphotransferases