Synthesis of chromeno[2,3-d]imidazol-9(1H)-ones via tandem reactions of 3-iodochromones with amidines involving copper-catalyzed C-H functionalization and C-O bond formation.
A novel six-membered heterocyclic skeleton of imidazochromone was prepared via an efficient one-pot reaction including a key step of copper-catalyzed aerobic C-H intramolecular cycloetherification. Notably, this process does not require the presence of strong para electron-withdrawing groups on the phenol component. Also, the results of this effort show that acyl phenols containing electron-rich heterocycles participate in an efficient C-H activation/C-O formation process.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 ZuChongZhi Road, Shanghai 201203, People's Republic of China.
Jia
J
Sheng
Bo
B
Chao
Hong
H
Chen
Youhong
Y
Hu
D000578:Amidines / Q000737:chemistry; D002384:Catalysis; D002867:Chromones / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry
D000578:Amidines; D002867:Chromones; D006575:Heterocyclic Compounds, 3-Ring; D007093:Imidazoles; D019800:Phenol; D003300:Copper