Rapid access to 3-(aminomethyl)isoquinoline-fused polycyclic compounds by copper-catalyzed four-component coupling, cascade cyclization, and oxidation.
A novel copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline-fused polycyclic compounds, through four-component coupling, cyclization, and oxidation, has been developed. A Mannich-type reaction of 2-ethynylbenzaldehyde with paraformaldehyde and a secondary amine followed by treatment with a diamine component gave tricyclic isoquinolines through cascade cyclization and oxidation. Construction of fused isoquinolines of various ring sizes is also presented.
Ohta
Yusuke
Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Kubota
Yushi
Y
Watabe
Tsuyoshi
T
Chiba
Hiroaki
H
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007546:Isoquinolines / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000737:chemistry*
C552374:3-(aminomethyl)isoquinoline; D000447:Aldehydes; D000588:Amines; D007546:Isoquinolines; D011083:Polycyclic Compounds; D003300:Copper